Hemp powder

ABSTRACT

A relatively dry, relatively free flowing cannabinoid concentrate composition having a plant extract and a thickening agent. The cannabinoid concentrate composition may have a variety of cannabinoids, drying agents, flowing agents, and/or stabilization agents. The mixture may be a dry powder formulation similar to the consistency of flour or sand. The mixture may comprise a cannabinoid raffinate, an isolated cannabinoid, maltodextrin, and or silica.

CLAIM OF PRIORITY

This application is claims priority to U.S. provisional application Ser. No. 62/624,658, filed Jan. 31, 2018, entitled “HEMP POWDER”; and U.S. provisional application Ser. No. 62/653,321, filed on Apr. 5, 2018, entitled “RAFFINATE FORMULATIONS”, which applications are incorporated herein by reference in their entirety.

BACKGROUND

Cannabis plant material contains a variety of potentially valuable compounds. For example tetrahydrocannabinol (THC), cannabidiol (CBD), cannabichromene (CBC), cannabigerol (CBG), cannabinol (CBN), and other compounds are present in varying amounts in cannabis and hemp plant material. Indeed, the combination of these compounds as found in the natural cannabis plant is potentially valuable over each compound individually.

Raw cannabis oil containing these and other compounds may be extracted from the cannabis flower/plant using techniques such as CO₂ extraction, or liquid-solid solvent extraction. The resulting product, however, is a tacky and sticky oil that is highly viscous and difficult to work with, especially when attempting to incorporate the compounds into topical, edible, or pharmaceutical products.

Additionally, the raw cannabis oil typically contains THC levels above 0.3% by mass, which is unlawful in certain jurisdictions. Moreover, the high content of THC in cannabis oil renders the oil unsuitable for many applications where the psychotropic effects of THC are undesirable. As such, it remains desirous to produce a product that is easier to work with (e.g., is less viscous, sticky, and/or tacky) that maintains some or all of the non-THC compounds.

It is with respect to these and other considerations that the technology is disclosed. Also, although relatively specific problems have been discussed, it should be understood that the embodiments presented should not be limited to solving the specific problems identified in the introduction.

SUMMARY

This Summary is provided to introduce a selection of concepts in a simplified form that are further described below in the Detailed Description. This Summary is not intended to identify key factors or essential features of the claimed subject matter, nor is it intended to be used to limit the scope of the claimed subject matter.

The technology described herein includes systems and methods to derive a dry-hemp powder that includes various compounds such as one or more of tetrahydrocannabinol (THC), cannabidiol (CBD), cannabichromene (CBC), cannabigerol (CBG), cannabinol (CBN), and/or terpenes.

In aspects of the technology, the dry-hemp powder may be a free flowing powder. Clumping of the powder may be non-existent or limited. In aspects of the technology, the powder may be capable of being used in conjunction with a powder sprayer.

Methods to produce the dry hemp powder may include providing a mixture. The mixture may include a polysaccharide, such as maltodextrin and/or starch, may be added. In aspects of the technology the dextrose equivalent of the maltodextrin is between 5 and 20 DE.

Additionally, one or more of a cannabinoid isolate, such as cannabidiol (CBD), cannabichromene (CBC), cannabigerol (CBG), cannabinol (CBN) may be added to the mixture.

Further, an acid may be added to the mixture. In aspects, the acid may be one of citric acid, lactic acid, or other suitable acid. This may include, in aspects of the technology, a weak organic acid. Additionally, a mineral ascorbate may be added to the mixture. The mineral ascorbate may be one of sodium ascorbate, calcium ascorbate, potassium ascorbate, and magnesium ascorbate. Carbonates may also be added, such as calcium carbonate. A drying and/or flow agent may also be added. For example, silica Nu-FLOW™, and/or other flow agent may be added. The mixture may be homogenized by rapidly blending the mixture. This forms a homogenized mixture. The homogenized mixture may then be combined with THC Reduced Raffinate (further described below) or other raffinate, isolate, or composition. The resulting formulation may then be blended. In aspects of the technology, the formulation may then be cooled and re-blended. Cooling after, during, or prior to blending may remove or reduce clumping of the resulting formulation.

The resulting dry-hemp powder may comprise one or more of the cannabinoids: cannabidiol (CBD), cannabichromene (CBC), cannabigerol (CBG), cannabinol (CBN). Each of these compounds may be introduced via the THC Reduced Hemp Raffinate. In aspects where a CBD, CBG, and/or CBN (“crystalized cannabinoid isolates) are added, the total % of raffinate may be less than 25.7%.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates a liquid chromatography system;

FIG. 2 illustrates a liquid chromatographic method for extracting one or more compounds from raw cannabis oil;

FIG. 3 illustrates a method for concentrating one or more fractions.

FIG. 4 illustrates analytical HPLC-MS chromatograms a combined standard of CBD and THC.

FIG. 5 illustrates analytical HPLC-MS chromatograms of crude oil.

FIG. 6 illustrates analytical HPLC-MS chromatograms of diluted raw cannabis oil.

FIG. 7 illustrates analytical HPLC-MS chromatograms for a combined fraction extracted from sample cannabis oil.

FIG. 8 illustrates analytical HPLC-MS chromatogram for a combined and diluted sample cannabis oil.

FIG. 9 illustrates analytical HPLC-MS chromatogram for isolate A.

FIG. 10 illustrates a preparative chromatogram of a normal phase separation method monitored at 220 nm and 240 nm where eluate from 0-6 CVs is pooled with 9-12 CVs to provide a clean cannabis oil following rotoevaporation, where the clean cannabis oil exhibits about 68% CBD and not more than 0.3% THC. Fractions 21-30, or about 6-7.5 CVs are pooled, evaporated, and recrystallized to provide a CBD isolate with about 95.1% CBD, as shown in Example 1.

FIG. 11 illustrates a preparative chromatogram of a normal phase separation method of raw cannabis oil described in Example 2.

FIG. 12 illustrates a preparative reverse phase separation method of raw cannabis oil described in Example 3.

FIG. 13 is a method to produce full spectrum hemp powder.

DETAILED DESCRIPTION Definitions

The terminology used in the disclosure herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the disclosure. As used in the description of the embodiments of the disclosure and the appended claims, the singular forms “a”, “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. Also, as used herein, “and/or” refers to and encompasses any and all possible combinations of one or more of the associated listed items. Furthermore, the term “about,” as used herein when referring to a measurable value such as an amount of a compound, amount, dose, time, temperature, and the like, is meant to encompass variations of 20%, 10%, 5%, 1%, 0.5%, or even 0.1% of the specified amount. It will be further understood that the terms “comprises” and/or “comprising,” when used in this specification, specify the presence of stated features, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof. Unless otherwise defined, all terms, including technical and scientific terms used in the description, have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs.

Aspects of the technology relate to dry powder or semidry compositions of cannabinoid containing powder. In aspects of the technology, raffinate hemp oil is mixed with one or more of a thickening agent, a drying agent, a stabilization agent, a flow agent, and/or a preserving agent. The relative percentage of cannabinoids may be adjusted by further adding one or more of tetrahydrocannabinol (THC, d9-THC, 1-trans-delta9-tetrahydrocannabinol), cannabidiol (CBD), Cannabigerol (CBG), Cannabichromene (CBC), Cannabicyclol (CBL), Cannabinol (CBN), Cannabivarin (CBV), delta-9 Tetrahydrocannabinolic acid (THCA, d9-THCA), Tetrahydrocannabivarin (THCV), Cannabidiolic acid (CBDA), Cannabigerolic acid (CBGA), Cannabidivarin (CBDV), Cannabichromevarin (CBCV), Cannabigerovarin (CBGV), and Cannabigerol Monomethyl Ether (CBGM). The resulting composition may then be mechanical mixed to form a dry or semidry powder.

One aspect of the technology is directed to a cannabinoid containing concentrate composition comprising about 10 to about 90 wt. %, about 30 to about 90 wt. %, or about 60 to about 90 wt. % Cannabichromene and less than about 5 wt. %, less than about 1 wt. %, less than about 0.5 wt. %, or less than about 0.3 wt. % tetrahydrocannabinol. The composition may be free or substantially free of tetrahydrocannabinol. The concentrate may be an oil or a powder. The concentrate may optionally include a drying agent. This composition is preferably derived from natural, plant sources and not from a combination of synthetic materials. The composition optionally further comprises about 5 to about 25 wt. %, or about 10 to about 20 wt. % fatty acids and terpenes. A method for making a cannabinoid containing concentrate composition comprising about 10 to about 90 wt. %, about 30 to about 90 wt. %, or about 60 to about 90 wt. % Cannabichromene and less than about 5 wt. %, less than about 1 wt. %, less than about 0.5 wt. %, or less than about 0.3 wt. % tetrahydrocannabinol is also disclosed. The method may be the THC REM, CBD ISO, or CBG/CBC methods disclosed herein.

One aspect of the technology is directed to a cannabinoid containing concentrate composition comprising about 10 to about 90 wt. %, about 20 to about 90 wt. %, or about 50 to about 90 wt. % Cannabigerol and less than about 5 wt. %, less than about 1 wt. %, less than about 0.5 wt. %, or less than about 0.3 wt. % tetrahydrocannabinol. The composition may be free or substantially free of tetrahydrocannabinol. The concentrate may be an oil or a powder. The concentrate may optionally include a drying agent. This composition is preferably derived from natural, plant sources and not from a combination of synthetic materials. The composition optionally further comprises about 5 to about 25 wt. %, or about 10 to about 20 wt. % fatty acids and terpenes. A method for making a cannabinoid containing concentrate composition comprising about 10 to about 90 wt. %, about 20 to about 90 wt. %, or about 50 to about 90 wt. % Cannabigerol and less than about 5 wt. %, less than about 1 wt. %, less than about 0.5 wt. %, or less than about 0.3 wt. % tetrahydrocannabinol is also disclosed. The method may be the THC REM, CBD ISO, or CBG/CBC methods disclosed herein.

One aspect of the technology is directed to a cannabinoid containing concentrate composition comprising about 10 to about 90 wt. %, about 30 to about 90 wt. %, or about 60 to about 90 wt. % of a combination of Cannabichromene and Cannabigerol and less than about 5 wt. %, less than about 1 wt. %, less than about 0.5 wt. %, or less than about 0.3 wt. % tetrahydrocannabinol. The composition may be free or substantially free of tetrahydrocannabinol. The concentrate may be an oil or a powder. The concentrate may optionally include a drying agent. This composition is preferably derived from natural, plant sources and not from a combination of synthetic materials. The composition optionally further comprises about 5 to about 25 wt. %, or about 10 to about 20 wt. % fatty acids and terpenes. A method for making a cannabinoid containing concentrate composition comprising about 10 to about 90 wt. %, about 30 to about 90 wt. %, or about 60 to about 90 wt. % of a combination of Cannabichromene and Cannabigerol and less than about 5 wt. %, less than about 1 wt. %, less than about 0.5 wt. %, or less than about 0.3 wt. % tetrahydrocannabinol is also disclosed. The method may be the THC REM, CBD ISO, or CBG/CBC methods disclosed herein.

One aspect of the technology is directed to a cannabinoid containing concentrate composition comprising 10-100 wt. %, 20-100 wt. %, 50-100 wt. %, or 60-100 wt. % Cannabidiol and less than 5 wt. %, less than 1 wt. %, less than 0.5 wt. %, or less than 0.3 wt. % tetrahydrocannabinol. The composition may be free or substantially free of tetrahydrocannabinol. The concentrate may be an oil or a powder. The concentrate may optionally include a drying agent. This composition is preferably derived from natural, plant sources and not from a combination of synthetic materials. The composition optionally further comprises 5-25 wt. %, or 10-20 wt. % fatty acids and terpenes. A method for making a cannabinoid containing concentrate composition comprising 10-100 wt. %, 20-100 wt. %, 50-100 wt. %, or 60-100 wt. % Cannabidiol and less than 5 wt. %, less than 1 wt. %, less than 0.5 wt. %, or less than 0.3 wt. % tetrahydrocannabinol is also disclosed. The method may be the THC REM, CBD ISO, or CBG/CBC methods disclosed herein.

One aspect of the technology is directed to a tetrahydrocannabinol concentrate composition comprising about 0.3 to about 20 wt. %, about 0.5 to about 20 wt. %, about 1 to about 20 wt. %, or about 1 to about 15 wt. % tetrahydrocannabinol. The composition may further comprise about 5 to about 25 wt. %, or about 10 to about 20 wt. % fatty acids and terpenes and/or about 10 to about 95 wt. % cannabinoids selected from the group comprising cannabidiol, Cannabigerol, Cannabichromene, Cannabicyclol, Cannabinol, Cannabivarin, delta-9 Tetrahydrocannabinolic acid, Tetrahydrocannabivarin, Cannabidiolic acid, Cannabigerolic acid, Cannabidivarin, Cannabichromevarin, Cannabigerovarin, Cannabigerol Monomethyl Ether and combination thereof. The concentrate may be an oil or a powder. The concentrate may optionally include a drying agent. This composition is preferably derived from natural, plant sources and not from a combination of synthetic materials. A method for making a cannabinoid containing concentrate composition comprising about 0.3 to about 20 wt. %, about 0.5 to about 20 wt. %, about 1 to about 20 wt. %, or about 1 to about 15 wt. % tetrahydrocannabinol is also disclosed. The method may be the THC REM, CBD ISO, or CBG/CBC methods disclosed herein.

Production of THC Reduced Raffinate and Other Raffinates

Raffinates, isolates, and other hemp derived compositions as described herein may be used to form the hemp powder as described further herein. The technology includes systems and methods to extract various compounds from raw cannabis oil. For example, a liquid chromatography system may be used to extract specific compounds from raw cannabis oil.

In an embodiment, the technology relates to a method for extracting compounds from raw cannabis oil. Raw cannabis oil, in aspects of the technology, is derived using the LE Method, which is as follows. Cannabis flower is transferred to a hammer mill where the flower is milled into a fine powder. This hammer milled raw cannabis powder is then transferred to the pellet mill where the hammer milled raw cannabis powder is compressed into approximately 2 cm×0.5 cm pellets. These raw cannabis pellets are then transferred to an extraction column. The extraction column is then filled with acetone (2.9:1 lbs of raw cannabis pellets:L of acetone). The raw cannabis pellets are soaked in acetone for 3 hours, and then the dark brown-green acetone/raw cannabis extract is pumped into a receiving container. Fresh acetone is pumped into the column containing raw cannabis pellets, and the soak process is repeated for another 3 hours. Then the acetone/raw cannabis extract is combined with the acetone/raw cannabis extract from the first extraction. Fresh acetone is pumped into the column containing raw cannabis pellets, and the soak process is repeated for another 3 hours. Then the acetone/raw cannabis extract is combined with the acetone/raw cannabis extract from the first and second extractions. After this third soak process, the combined acetone/raw cannabis extract is then concentrated under vacuum at 50° C. The remaining raw cannabis oil is a viscous dark-brown green mixture.

Other methods of producing raw cannabis oil are known and may be used in conjunction with the technology described herein. For example CO2 extraction methods and other methods are known. See, e.g., U.S. Pat. No. 8,895,078, Method for Producing and Extract from Cannabis Plant Matter, Containing a Tetrahydrocannabinol and a Cannabidiol and Cannabis Extracts to Mueller, filed Oct. 16, 2003; Chinese Patent Publication Number 105505565A, Method for Extracting Industrial Hemp Oil Rich in Cannabidiol to

(Tengchunjuan) et al., filed Dec. 28, 2015.

In some embodiments, a preparatory method is provided for removing one or more cannabis compounds from a cannabis oil, the method comprising: obtaining a column packed with a stationary phase particulate; adding cannabis oil to the packed column; adding a first eluent to the packed column; adding a second eluent to the packed column; collecting at least two eluate fractions comprising one or more compounds; disposing of at least one of the at least two eluate fractions; and evaporating at least one of the remaining at least two fractions to form a composition. In some embodiments, the method comprises adding a third eluent is to the packed column.

In embodiments, the stationary phase particulate is selected from normal phase or reverse phase stationary phase. In a specific embodiment, the column is a normal phase silica gel stationary phase column. In other embodiments, a reverse phase stationary phase is selected from the group consisting of C18, C8, C4 and phenyl stationary phase particulate.

In some embodiments, a normal phase column is employed, and a mobile phase comprising a first eluent and second eluent are used to elute the column. In some embodiments, the first eluent and second eluent are different and each is selected from one or more of petroleum ether, pentane, n-hexane, hexanes, diethyl ether, ethyl acetate, and ethanol. In some embodiments, the first eluent and the second eluent are each solvents selected from one or, or a specific mixture of two or more of, the group consisting of petroleum ether, pentane, n-hexane, hexanes, diethyl ether, ethyl acetate, and ethanol. In some embodiments, the first eluent and second eluent are each solvents selected from one of, or a specific mixture of two or more of, the group consisting of petroleum ether, pentane, n-hexane, hexanes, n-heptane, heptanes, diethyl ether, methyl tert butyl ether, ethyl acetate, and ethanol.

In embodiments, the first eluent and the second eluent are each solvents selected from one of, or a specific mixture of two or more of, the group consisting of petroleum ether, n-hexane, hexanes, n-heptane, heptanes, diethyl ether, and methyl tert butyl ether. In embodiments, the first eluent and the second eluent are each a mixture of diethyl ether and petroleum ether. In embodiments, the first eluent and the second eluent are each a mixture of methyl tert butyl ether and petroleum ether. In embodiments, the first eluent and the second eluent are each a mixture of diethyl ether and n-heptane or a heptane. In embodiments, the first eluent and the second eluent are each a mixture of methyl tert butyl ether and n-heptane or a heptane.

In some embodiments, the normal phase column is eluted with a first eluent solvent system selected from 90-97 vol % petroleum ether with 3-10 vol % of a mixture of from 90-100 vol % diethyl ether with 0-10 vol % ethanol; 90-97 vol % pentane with 3-10 vol % of a mixture of a mixture of from 90-100 vol % diethyl ether with 0-10 vol % ethanol; 90-97 vol % n-hexane with 3-10% of a mixture of from 90-100 vol % diethyl ether with 0-10 vol % ethanol.

In some specific embodiments, the normal phase column is eluted with a first eluent solvent system selected from 92 vol % petroleum ether and 8 vol % of a mixture of 95% diethyl ether/5% ethanol; 92 vol % pentane and 8 vol % of a mixture of 95% diethyl ether/5% ethanol; 92 vol % n-hexane and 8 vol % of a mixture of 95% diethyl ether/5% ethanol; 96 vol % petroleum ether and 4 vol % of a mixture of 95% diethyl ether/5% ethanol; 96 vol % pentane and 4 vol % of a mixture of 95% diethyl ether/5% ethanol; or 96 vol % n-hexane and 4 vol % of a mixture of 95% diethyl ether/5% ethanol.

In some embodiments, the normal phase column is eluted with a second eluent solvent system selected from: 60-80 vol % petroleum ether with 20-40 vol % of a mixture of from 90-100 vol % diethyl ether/0-10 vol % ethanol; 60-80 vol % pentane with 20-40 vol % of a mixture of a mixture of from 90-100 vol % diethyl ether/0-10 vol % ethanol; or 60-80 vol % n-hexane with 20-40 vol % of a mixture of from 90-100 vol % diethyl ether/0-10 vol % ethanol.

In some specific embodiments, the normal phase column is eluted with a second eluent solvent system selected from: 70 vol % petroleum ether and 30% of a mixture of 95% diethyl ether/5% ethanol; 70 vol % pentane and 30 vol % of a mixture of 95% diethyl ether/5% ethanol; 70 vol % n-hexane and 30 vol % of a mixture of 95% diethyl ether/5% ethanol; 60 vol % petroleum ether and 40 vol % of a mixture of 95% diethyl ether/5% ethanol; 60 vol % pentane and 40 vol % of a mixture of 95% diethyl ether/5% ethanol; or 60 vol % n-hexane and 40 vol % of a mixture of 95% diethyl ether/5% ethanol.

In embodiments, the second eluent is selected from 30-40 vol % water with 0.05-1 vol % formic acid and 70-60 vol % ethanol with 0.05-1 vol % formic acid; or 30-40 vol % water with 0.05-1 vol % formic acid and 70-60 vol % acetonitrile with 0.05-1 vol % formic acid.

In embodiments, the second eluent is selected from 20-30 vol % water with 0.05-1 vol % formic acid and 70-80 vol % ethanol with 0.05-1 vol % formic acid; or 20-30 vol % water with 0.05-1 vol % formic acid and 70-80 vol % acetonitrile with 0.05-1 vol % formic acid.

In some specific embodiments, the normal phase column is eluted with a first eluent in a volume of between one and eleven column volumes (CVs), 2 to 7 CVs, or 4 to 6 CVs; and a second eluent in a volume of between one and eleven column volumes (CVs), 2 to 7 CVs, or 4 to 6 CVs.

In some embodiments, a reverse phase column is employed and a mobile phase comprising a first eluent and second eluent are used to elute the column. In some embodiments, the first eluent and second eluent are different and each is selected from one or more of water, acetonitrile, and ethanol, with or without an acidic modifier. In some embodiments, the reverse phase stationary phase column is eluted with a first eluent selected from 30-40 vol % water and 70-60 vol % ethanol optionally containing an organic acid modifier selected from formic acid or trifluoroacetic acid in from 0.01-0.2 vol %; or 30-40 vol % water and 70-60 vol % acetonitrile; wherein the first eluent optionally containing an organic acid modifier selected from formic acid or trifluoroacetic acid in from 0.01-0.2 vol %.

In some specific embodiments, the reverse phase column is eluted with a second eluent selected from 20-30 vol % water and 70-80 vol % ethanol; or 20-30 vol % water and 70-80 vol % acetonitrile, optionally wherein the first and second eluent contain an organic acid modifier selected from formic acid or trifluoroacetic acid in from 0.01-0.2 vol %.

In one embodiment, the method comprises pooling the normal phase eluate from 6-7.5 column volumes, evaporating the pooled eluate to form a composition, and recrystallizing the composition to provide a purified composition comprising cannabidiol (CBD) in greater than 94% purity, having not more than 0.3% THC. In embodiments, the purified composition comprises CBD after recrystallization having at least 94% purity. In embodiments, the purified composition comprises CBD after recrystallization having at least 95% purity. In embodiments, the purified composition comprises CBD after recrystallization having at least 96% purity. In embodiments, the purified composition comprises CBD after recrystallization having at least 97% purity. In embodiments, the purified composition comprises CBD after recrystallization having at least 98% purity. In embodiments, the purified composition comprises CBD after recrystallization having at least 99% purity. In embodiments, the purified composition comprises CBD after recrystallization having 100% purity. In embodiments, after evaporation and prior to recrystallization the composition comprises CBD having a purity of 90-95%. In some embodiments, the CBD is recrystallized from pentane, n-hexane, petroleum ether, or a mixture thereof.

In some embodiments, the method comprises pooling the normal phase eluate from 1-6 and 9-12 CVs, and evaporating to provide a composition comprising 60-75% CBD, 0.001-0.5% THC, 0.1-8% CBC, CBG, CBN, and about 5-25% fatty acids and terpenes. In some embodiments, the composition comprises 65-70% CBD, not more than 0.3% THC, 0.3-5% CBC, 0.3-5% CBG, 0.3-5% CBN, and about 10-20% fatty acids and terpenes. In some embodiments, the composition comprises 65-70% CBD, not more than 0.2% THC, 0.3-5% CBC, and about 15% fatty acids and terpenes.

In another embodiment, a method is provided for processing raw cannabis oil to provide clean cannabis oil, or a CBD isolate, having less than 0.3 wt % delta9-THC, the method comprising: obtaining raw cannabis oil; applying the raw cannabis oil to a normal stationary phase column; eluting the normal stationary phase column with a binary solvent system wherein the binary solvent system comprises a first solvent A and a second solvent B; fractionating the eluate into at least two eluate fractions; disposing at least one of the at least two eluate fractions; and evaporating the solvent from the remaining at least two eluate fractions to provide the clean cannabis oil comprising less than 0.3 wt % THC. In a specific embodiment, the normal stationary phase column is a silica gel column.

In some embodiments, the raw cannabis oil is obtained by supercritical CO₂ extraction of Cannabis spp. plant material, solvent-solid extraction of Cannabis spp. plant material, or from a commercial supplier.

In some embodiments, the first solvent A in the binary solvent system is a non-polar solvent selected from one or more of the group consisting of pentane, petroleum ether, hexanes, n-hexane, heptane, diisopropyl ether, toluene, chloroform, and methylene chloride; preferably petroleum ether, hexanes, or n-hexane. In embodiments, the first solvent A in the binary solvent system is a non-polar solvent selected from one or more of the group consisting of pentane, petroleum ether, hexanes, n-hexane, n-heptane, heptanes, diisopropyl ether, toluene, chloroform, and methylene chloride. In embodiments, the first solvent A in the binary solvent system is petroleum ether, a heptane, or n-heptane.

In some embodiments, the second solvent B in the binary solvent system is a polar solvent selected from one or more of the group consisting of diethyl ether, tetrahydrofuran, ethyl acetate, acetone, acetonitrile, isopropanol, ethanol, and methanol; preferably diethyl ether, a mixture of diethyl ether and ethanol, or ethyl acetate. In embodiments, the second solvent B in the binary solvent system is a polar solvent selected from one or more of the group consisting of diethyl ether, methyl tert butyl ether, tetrahydrofuran, ethyl acetate, acetone, acetonitrile, isopropanol, ethanol, and methanol. In embodiments, the polar solvent is diethyl ether or methyl tert butyl ether.

In some embodiments, the normal phase column is eluted with a step gradient using a binary solvent system comprising the first solvent A and the second solvent B, wherein solvent A is petroleum ether, pentane, or n-hexane and the solvent B is a mixture of 90-100:0-10 v/v diethyl ether/ethanol. In a specific embodiment, the column is eluted with a mixture of solvent A/solvent B at 8% solvent B for 7 CV, then 30% solvent B for 6 CV. In embodiments, the column is eluted with a step gradient using a binary solvent system comprising the first solvent A and the second solvent B, wherein solvent A is petroleum ether, a heptane, or n-heptane and solvent B is diethyl ether or methyl tert butyl ether.

In some embodiments, the normal phase column is eluted and eluate from 0-6 column volumes and 9-12.5 column volumes are pooled, and concentrated to provide clean cannabis oil having not more than 0.3 wt % THC and about 60-70 wt % CBD.

In specific embodiments, the yield of clean cannabis oil is not less than 60 wt %, or not less than 65 wt % based on starting raw cannabis oil.

In embodiments, the solvent A is petroleum ether, solvent B is 95% diethyl ether and 5% ethanol, and the eluate fractions from 0-6 column volumes and 9-12 column volumes are pooled, and concentrated to provide clean cannabis oil having not more than 0.3 wt % THC and about 60-70 wt % CBD.

In embodiments, applying the method comprises loading 1 to 20 wt %, 2 to 15 wt %, or 4 to 8 wt % of the raw cannabis oil to the normal stationary phase column, when compared to the total weight of the normal stationary phase.

In a specific embodiment, the disclosure provides a composition comprising about 65-70% CBD, not more than 0.3% THC, 0.3-5% CBC, 0.3-5% CBG, 0.3-5% CBN, and about 10-20% fatty acids and terpenes. Also disclosed herein is a composition comprising about 40-80% CBD, not more than 0.3% THC, 0.3-5% CBC, 0.3-5% CBG, and 0.3-5% CBN.

Also disclosed herein are processes that can concentrate cannabidiol (CBD) from a cannabis oil prior to performing the chromatography methods disclosed herein. A method of concentrating CBD from a cannabis oil disclosed herein comprises: mixing petroleum ether with a heated cannabis oil to provide a mixture; allowing the mixture to cool to room temperature; cooling the mixture to 0° C. to provide a cooled mixture; mixing a first amount of petroleum ether at −10° C. to 0° C. into the cooled mixture; freezing the cooled mixture for at least two hours or cooling the cooled mixture at 0° C.; adding a second amount of petroleum ether at −10° C. to 0° C. to the mixture; filtering the mixture to provide a filtrate and a concentrate; and collecting the concentrate, wherein the concentrate comprises CBD having at least about 94% purity and the concentrate has not more than 0.3% THC. In embodiments, the concentrate comprises CBD having 90-95% purity.

In embodiments, the cooled mixture is frozen for 2-24 hours or 6-24 hours, for example, for 2-18 hours or for 6-18 hours.

In embodiments, the concentrate does not include THC. In embodiments, the concentrate does not include CBG. In embodiments, the concentrate does not include CBC. In embodiments, the concentrate does not include CBN. As used herein, in embodiments, “does not include” means that the component is below a detectable limit.

In embodiments, the method further comprises performing a recrystallization of the concentrate after collecting the concentrate, wherein the recrystallization provides CBD having greater than 95% purity. In embodiments, the recrystallization provides CBD having at least 98% purity. In embodiments, the recrystallization provides CBD having at least 99% purity. In embodiments, the recrystallization provides CBD having at least 99.5% purity. In embodiments, the recrystallization provides CBD having 100% purity. The recrystallization can involve one or more recrystallization steps. In embodiments, the recrystallization in a single recrystallization. In embodiments, the recrystallization is two recrystallizations.

In embodiments, filtering the mixture comprises filtering the mixture both at atmospheric pressure and under vacuum.

In embodiments, the method further comprises collecting the filtrate, wherein the filtrate contains CBD in an amount from about 20 wt % to about 70 wt % less than CBD present in the cannabis oil. For example, the filtrate can contain CBD in an amount from about 20 wt % to about 50 wt %, from about 40 wt % to about 60 wt %, or from about 45 wt % to about 60 wt %.

Further disclosed herein are processes that take a cannabinoids fraction arising from the chromatography methods disclosed herein and provide CBG, CBC, or a mixture thereof from the cannabinoids fraction.

According to a method, a cannabinoids fraction (e.g., provided as a product of the chromatography methods disclosed herein) is subjected to mixing ethanol at 50-70° C. into the cannabinoids fraction to provide a mixture; performing reverse phase chromatography on the mixture providing multiple CVs; identifying CVs containing CBG; concentrating the CVs containing CBG; and recrystallizing CBG, wherein the CBG has a purity of at least 94%. In embodiments, the CBG is not recrystallized. In these embodiments, concentrating the CVs containing CBG provides an oil containing CBG having a purity of at least 90%.

According to a method, a cannabinoids fraction (e.g., provided as a product of the chromatography methods disclosed herein) is subjected to mixing ethanol at 50-70° C. into the cannabinoids fraction to provide a mixture; performing reverse phase chromatorgraphy on the mixture providing multiple CVs; identifying CVs containing CBC; and concentrating the CVs containing CBC to provide a CBC oil. In embodiments, the CBC oil has a purity from 94%-96%. In embodiments, the CBC oil has a purity from 90-96%.

When the CBG is not recrystallized, the oil containing CBG and the oil containing CBC can be recombined to provide a mixture comprising CBC and CBG.

According to a method, a cannabinoids fraction (e.g., provided as a product of the chromatography methods disclosed herein) is subjected to mixing ethanol at 50-70° C. into the cannabinoids fraction to provide a mixture; performing reverse phase chromatography on the mixture providing multiple CVs; identifying CVs containing CBG and CBC; and concentrating the CVs containing CBG and CBC to provide an oil comprising CBG and CBC, wherein the CBG has a purity of at least 90%. In embodiments, the oil comprises CBC having a purity from 94-96%. In embodiments, the oil comprises CBC having a purity from 90-96%.

In embodiments, the CVs containing CBG are identified by thin layer chromatography. In embodiments, the CVs containing CBC are identified by thin layer chromatography. In embodiments, the CVs containing CBG and CBC are identified by thin layer chromatography.

In embodiments, performing reverse phase chromatography comprises: eluting a column with a first solvent for 3 CV; eluting the column with the first solvent for 4 CV; and eluting the column with a second solvent for 7 CV, wherein fractions collected from 2 CV to 3.5 CV contain CBG.

In embodiments, performing reverse phase chromatography comprises eluting a column with a first solvent for 3 CV; eluting the column with the first solvent for 4 CV; and eluting the column with a second solvent for 7 CV, wherein fractions collected from 6-9 CV contain CBC.

In embodiments, the first solvent is 80% methanol and 20% distilled water and the second solvent is 85% methanol and 15% distilled water.

In embodiments, performing reverse phase chromatography comprises eluting a column with a step gradient using a binary solvent system comprising a first solvent A and a second solvent B, wherein the solvent A is methanol, ethanol, or acetonitrile and the second solvent B is distilled water. In embodiments, the first solvent A is methanol and the second solvent B is distilled water.

Also disclosed herein is an oil containing CBG produced by these methods. Further disclosed herein is an oil containing CBC produced by these methods.

Additionally disclosed herein is a mixture comprising CBG and the CBC produced by these methods having less than 0.3% THC. In embodiments, the mixture comprising CBG and CBC does not include THC. Again, as used herein, in embodiments, “does not include” means that the component is below a detectable limit. The mixture can have a CBG content and a CBC content that is approximately equal. The mixture can have 50 wt % CBG and 50 wt % CBC.

In aspects of the technology, various compounds are extracted from bulk cannabis oil using liquid chromatography. These oils (i.e., a raffinate) may be added to form a hemp powder as further described below. For example, an extraction process, such as CO₂ extraction, or liquid-solid solvent extraction, is performed on cannabis plant material. In some embodiments, the resulting extract, referred to herein as raw cannabis oil or bulk cannabis oil, may contain a variety of cannabinoids and other substances. For example, tetrahydrocannabinol (THC, d9-THC, 1-trans-delta9-tetrahydrocannabinol), cannabidiol (CBD), Cannabigerol (CBG), Cannabichromene (CBC), Cannabicyclol (CBL), Cannabinol (CBN), Cannabivarin (CBV), delta-9 Tetrahydrocannabinolic acid (THCA, d9-THCA), Tetrahydrocannabivarin (THCV), Cannabidiolic acid (CBDA), Cannabigerolic acid (CBGA), Cannabidivarin (CBDV), Cannabichromevarin (CBCV), Cannabigerovarin (CBGV), and Cannabigerol Monomethyl Ether (CBGM) may be present in varying concentrations in the raw cannabis oil.

In some embodiments, a method is provided to remove or deplete a THC component from crude cannabis oil, industrial hemp extracts, or hemp oil to form a raffinate, which may be incorporated into the hemp powder. Accordingly, methods are provided to process crude cannabis oil, industrial hemp extract, or hemp oil, to provide a clean cannabis oil. In some embodiments, the clean cannabis oil comprises from 0.001-3 wt %, 0.01-2 wt %, or 0.1-0.3 wt % THC; or not more than 1.0 wt %, 0.5 wt %, 0.3 wt %, 0.2 wt %, 0.1 wt %, or 0.05 wt % THC. In other embodiments, a method is provided to remove or deplete THC from crude cannabis oil, or hemp oil, to provide a clean cannabis oil having a cannabinoid profile of about 40-70% CBD, 1-3% CBG, 1-3% CBC, 1-3% CBN, 1-5% CBDA, 1-5% THCA, and 10-30% fatty acids and terpenes, and not more than 3 wt %, 2 wt %, 0.8 wt %, 0.5 wt %, 0.4 wt %, 0.3 wt %, 0.2 wt %, 0.1 wt %, or 0.05 wt % THC.

In a specific embodiment, a method is provided to process crude cannabis oil, industrial hemp extracts, or hemp oil to provide a clean cannabis oil having not more than 70 wt % CBD and not more than 0.3 wt % THC. This oil (i.e., a raffinate) may be added to form a hemp powder as further described below. In some embodiments, the clean cannabis oil comprises 40-70 wt %, 50-70 wt %, 55-70 wt %, or 65-70 wt % CBD, and not more than 0.3 wt % THC. In a specific embodiment, the clean cannabis oil comprises 65-70% CBD, >0.3% THC, 0.3-5% CBC, CBG, CBN, and ˜15% fatty acids and terpenes. In some embodiments, a clean cannabis oil is provided containing from about 0.1-10 wt %, 0.5-8 wt %, 1-7 wt %, 2-6 wt %, or about 3-5 wt % terpenes comprising one or more, two or more or three or more terpenes selected from the group consisting of myrcene, linalool, limonene, beta-caryophyllene (beta-humulene), alpha-caryophyllene (alpha-humulene), alpha-pinene, beta-pinene, alpha-bisabolol, delta-3-carene, trans-gamma-bisabolene, borneol, terpineol, eucalyptol, trans-ocimene, trans-alpha-farnesene, cis-beta-farnesene, gamma-curcumene, beta-fenchol, fenchone, beta-phellandrene, guajol, alpha-guaiene, alpha-eudesmol, terpinolene, alpha-selinene, camphene, alpha-thujene, and cineole.

In some embodiments, a clean cannabis oil is provided comprising about 5-30 wt %, 6-25 wt %, 7-20 wt %, 8-15 wt %, or 9-12 wt % fatty acids, comprising both unsaturated fatty acids selected and saturated fatty acids. This oil (i.e., a raffinate) may be added to form a hemp powder as further described below. The clean cannabis oil may comprise one or more unsaturated fatty acids selected from linoleic acid, alpha-linolenic acid, oleic acid, gamma-linolenic acid, stearidonic acid, eicosanoic acid, cis-vaccenic acid, and isolinolenic acid. The clean cannabis oil may comprise one or more saturated fatty acids selected from palmitic acid, stearic acid, arachidonic acid, behenic acid, myristic acid, lignoceric acid, caproic acid, heptanoic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, margaric acid, and isoarachidic acid.

In other embodiments, a method is provided for processing crude cannabis oil to provide a CBD isolate enriched in CBD, compared to the starting raw cannabis oil. These isolates may be added to form a hemp powder as further described below. In some embodiments, the CBD isolate comprises CBD in from 70 wt %-99.99 wt %, 75-99.9 wt %, 80-99 wt %, 90-98 wt %, or 94-98 wt % CBD, or not less than 90 wt %, 94 wt %, 95 wt %, 97.5 wt %, 98 wt %, 99 wt %, 99.5 wt %, or not less than 99.9 wt % CBD, while comprising not more than 0.3 wt % of THC. In certain aspects, the CBD isolate contains not more than 1 wt %, 0.5 wt %, 0.3 wt % of any of THCV, THCV, CBC, CBN, CBG, THCA, CBDA, CBGA, and CBDV.

In some embodiments, the individual components are identified and/or quantified by any technique known in the art. For example, comparison to HPLC standards, HPLC, HPLC-MS, GC, GC-MS, IR, MS, ¹H-NMR, ¹³C-NMR, and/or elemental analysis.

In some embodiments, methods are provided herein for processing raw cannabis oil to allow for the isolation and or depletion of individual cannabinoid and custom formulation of over ten individual medicinally relevant cannabinoids selected from one or more, two or more, three or more, four or more, five or more, six or more, seven or more, or eight or more, or nine cannabinoids selected from the group consisting of CBD, THCV, D9-THC (THC), D8-THC, CBC, CBN, CBG, THCA, CBDA, CBGA, and CBDV. This isolates may be added to form a hemp powder as further described below.

In other embodiments, a method is provided for processing crude cannabis oil to provide a THCV isolate enriched in THCV, compared to the starting raw cannabis oil. This THCV isolate may be added to form a hemp powder as further described below. In some embodiments, the THCV isolate comprises THCV in from 70 wt %-99.99 wt %, 75-99.9 wt %, 80-99 wt %, 90-98 wt %, or 95-98 wt % THCV, or not less than 95 wt %, 97.5 wt %, 98 wt %, 99 wt %, 99.5 wt %, or not less than 99.9 wt % THCV, while comprising not more than 0.3 wt % of a cannabinoid selected from the group consisting of THC, CBD, CBC, CBN, CBG, THCA, CBDA, CBGA, and CBDV.

In other embodiments, a method is provided for processing crude cannabis oil to provide a THC isolate enriched in THC, compared to the starting raw cannabis oil. These isolates may be added to form a hemp powder as further described below. In some embodiments, the THC isolate comprises THC in from 70 wt %-99.99 wt %, 75-99.9 wt %, 80-99 wt %, 90-98 wt %, or 95-98 wt % THC, or not less than 95 wt %, 97.5 wt %, 98 wt %, 99 wt %, 99.5 wt %, or not less than 99.9 wt % THC, while comprising not more than 0.3 wt % of a cannabinoid selected from the group consisting of CBD, THCV, CBC, CBN, CBG, THCA, CBDA, CBGA, and CBDV.

In other embodiments, a method is provided for processing crude cannabis oil to provide a CBC isolate enriched in CBC, compared to the starting raw cannabis oil. These isolates may be added to form a hemp powder as further described below. In some embodiments, the CBC isolate comprises CBC in from 70 wt %-99.99 wt %, 75-99.9 wt %, 80-99 wt %, 90-98 wt %, or 95-98 wt % CBC, or not less than 95 wt %, 97.5 wt %, 98 wt %, 99 wt %, 99.5 wt %, or not less than 99.9 wt % CBC, while comprising not more than 0.3 wt % of a cannabinoid selected from the group consisting of CBD, THC, THCV, CBN, CBG, THCA, CBDA, CBGA, and CBDV.

In other embodiments, a method is provided for processing crude cannabis oil to provide a CBN isolate enriched in CBN, compared to the starting raw cannabis oil. These isolates may be added to form a hemp powder as further described below. In some embodiments, the CBN isolate comprises CBN in from 70 wt %-99.99 wt %, 75-99.9 wt %, 80-99 wt %, 90-98 wt %, or 95-98 wt % CBN, or not less than 95 wt %, 97.5 wt %, 98 wt %, 99 wt %, 99.5 wt %, or not less than 99.9 wt % CBN, while comprising not more than 0.3 wt % of a cannabinoid selected from the group consisting of THC. CBD, THCV, CBC, CBG, THCA, CBDA, CBGA, and CBDV.

In other embodiments, a method is provided for processing crude cannabis oil to provide a CBG isolate enriched in CBG, compared to the starting raw cannabis oil. In some embodiments, the CBG isolate comprises CBG in from 70 wt %-99.99 wt %, 75-99.9 wt %, 80-99 wt %, 90-98 wt %, or 95-98 wt % CBG, or not less than 95 wt %, 97.5 wt %, 98 wt %, 99 wt %, 99.5 wt %, or not less than 99.9 wt % CBD, while comprising not more than 0.3 wt % of a cannabinoid selected from the group consisting of THC, CBD, CBC, CBN, THCV, THCA, CBDA, CBGA, and CBDV.

In other embodiments, a method is provided for processing crude cannabis oil to provide a THCA isolate enriched in THCA, compared to the starting raw cannabis oil. These isolates may be added to form a hemp powder as further described below. In some embodiments, the THCA isolate comprises THCA in from 70 wt %-99.99 wt %, 75-99.9 wt %, 80-99 wt %, 90-98 wt %, or 95-98 wt % THCA, or not less than 95 wt %, 97.5 wt %, 98 wt %, 99 wt %, 99.5 wt %, or not less than 99.9 wt % THCA, while comprising not more than 0.3 wt % of a cannabinoid selected from the group consisting of THC, CBD, CBC, CBG, CBN, THCV, CBDA, CBGA, and CBDV.

In other embodiments, a method is provided for processing crude cannabis oil to provide a CBDA isolate enriched in CBDA, compared to the starting raw cannabis oil. These isolates may be added to form a hemp powder as further described below. In some embodiments, the CBDA isolate comprises CBDA in from 70 wt %-99.99 wt %, 75-99.9 wt %, 80-99 wt %, 90-98 wt %, or 95-98 wt % CBDA, or not less than 95 wt %, 97.5 wt %, 98 wt %, 99 wt %, 99.5 wt %, or not less than 99.9 wt % CBDA, while comprising not more than 0.3 wt % of a cannabinoid selected from the group consisting of THC, CBD, CBC, CBG, CBN, THCV, THCA, CBGA, and CBDV.

In other embodiments, a method is provided for processing crude cannabis oil to provide a CBGA isolate enriched in CBGA, compared to the starting raw cannabis oil. These isolates may be added to form a hemp powder as further described below. In some embodiments, the CBGA isolate comprises CBGA in from 70 wt %-99.99 wt %, 75-99.9 wt %, 80-99 wt %, 90-98 wt %, or 95-98 wt % CBGA, or not less than 95 wt %, 97.5 wt %, 98 wt %, 99 wt %, 99.5 wt %, or not less than 99.9 wt % CBGA, while comprising not more than 0.3 wt % of a cannabinoid selected from the group consisting of THC, CBD, CBC, CBG, CBN, THCV, THCA, CBDA, and CBDV.

In other embodiments, a method is provided for processing crude cannabis oil to provide a CBDV isolate enriched in CBDV, compared to the starting raw cannabis oil. These isolates may be added to form a hemp powder as further described below. In some embodiments, the CBDV isolate comprises CBDV in from 70 wt %-99.99 wt %, 75-99.9 wt %, 80-99 wt %, 90-98 wt %, or 95-98 wt % CBDV, or not less than 95 wt %, 97.5 wt %, 98 wt %, 99 wt %, 99.5 wt %, or not less than 99.9 wt % CBDV, while comprising not more than 0.3 wt % of a cannabinoid selected from the group consisting of THC, CBD, CBC, CBG, CBN, THCV, THCA, CBDA, and CBGA.

In some embodiments, a composition comprising CBD, CBC and terpenes is provided comprising not more than 0.3 wt % of THC. This composition may be added to form a hemp powder as further described below.

In some embodiments, a composition comprising CBD and fatty acids is provided comprising not more than 0.3 wt % of THC. This composition may be added to form a hemp powder as further described below.

In some embodiments, a composition comprising CBG and CBD is provided comprising not more than 0.3 wt % of THC. This composition may be added to form a hemp powder as further described below.

In a specific embodiment, a composition is provided comprising ˜65-70% CBD, 0.001-0.5% THC, 0.3-5% CBC, CBG, CBN, and ˜10-20% fatty acids and terpenes. This composition may be added to form a hemp powder as further described below. In some aspects, the composition is dependent on the input hemp extract; however, in the composition the THC content is significantly reduced compared to starting raw cannabis oil such that the composition comprises not more than 0.5%, 0.4%, 0.3%, 0.2% or 0.1% THC, while essentially leaving the profile of the complex mixture intact. In some embodiments, the individual compounds are isolated from the composition and quantified to verify their identity.

In some embodiments of the technology, raw cannabis oil is separated using preparative liquid chromatographic methods described further herein. However, in some embodiments, the eluate fractionation method is non-traditional in order to reconstitute most components of the starting raw cannabis oil to provide a clean cannabis oil, while significantly reducing the amount of THC compared to the starting raw cannabis oil, such that the concentration of THC in the clean cannabis oil is not more than 0.5, 0.4, 0.3, 0.2, 0.1, 0.05, 0.03, 0.01 wt % THC. For example, raw cannabis oil may be injected into a column and eluted in an isocratic, gradient, or a step-wise fashion. Fractions may be taken at (and for) specific column volumes (CVs). These fractions contain one or more compounds from the raw cannabis oil. Additionally, each fraction may be combined with at least one other fraction. Further, each fraction (or combination of fraction) may be concentrated using a variety of techniques as described further herein.

FIG. 1 illustrates a system 100 to perform a liquid chromatographic extraction, which may be used to produce the raffinates, the isolates, and the compositions. As illustrated, FIG. 1 includes a liquid chromatography column 102, a High Performance Liquid Chromatography Mass Spectrometry instrument (“HPLC-MS”) 104, and concentration station 108.

In some embodiments, the crude starting cannabis oil, or one or more fractions thereof, is isolated and/or purified by preparative chromatography. Liquid chromatography column 102 includes a column 110. In aspects, the column 110 has a volume of 990 mL, with a height of 291 mm and a diameter of 82 mm. As illustrated, the column 110 is packed with a material 112, such a silica gel for normal phase, or phenyl, C4, C8 or C18 for reverse phase. Additionally, the column may be pre-wet by adding the pre-wetting solvent (such as water, petroleum ether, diethyl ether or ethanol) into the column prior to the injection of cannabis oil sample 114.

The cannabis oil sample 114 may be raw cannabis oil, or hemp oil, obtained from bulk extraction of Cannabis spp. plant material. Extraction of cannabis or hemp plant material may be performed using super critical CO₂ extraction, liquid-solvent extraction, or other techniques known in the art to provide bulk cannabis oil, also known as crude cannabis oil, or raw cannabis oil. In aspects of the technology, the bulk cannabis oil may contain approximately 30-60% CBD, 3-5% THC, 1-3% CBG, 1-3% CBC, 1-3% CBN, 1-5% CBDA, 1-5% THCA, and 15-30% fatty acids and terpenes.

In some embodiments, raw cannabis oil is first diluted to form the cannabis oil sample 114. For example, for a process employing a normal phase silica gel stationary phase column, the raw cannabis oil may be mixed with a non-polar solvent prior to loading the column. In specific embodiments, the non-polar solvent is hexanes, n-hexane, pentane or petroleum ether. For example, the raw oil can be diluted in a two parts cannabis oil to one part petroleum ether, pentane, hexanes, or n-hexane to form the cannabis oil sample 114. In alternative embodiments, when employing a reverse phase stationary phase column, the raw cannabis oil may be dissolved in ethanol and diluted with water prior to loading to the column. mixed in equal parts with ethanol.

The cannabis oil sample 114 is injected into the column 110 using a pipette or other technique known in the art. In aspects of the technology, the cannabis oil sample 114 is injected into the column 110 in an amount selected from 1 to 20 wt %, 2 to 15 wt % or 4 to 8 wt %, of the stationary phase material by weight. After the cannabis oil sample 114 is injected into the column 110, one or more eluents 116 may be added to the column 110 to extract one or more compounds from the cannabis oil sample 114. A first volume of a first eluent may be added, followed by a second volume of a second eluent and so on. In various embodiments, the eluents are selected from one or more solvents, or one or more binary mixtures of solvents may be used to elute a normal phase column.

In one embodiment, the normal phase column is a silica gel column which may be eluted with a non-polar solvent, a polar solvent, or a mixture of two or more, three or more, or four or more solvents. In one embodiment, a mixture of one or more non-polar solvents and one or more polar solvents is employed to elute the normal phase column.

In some embodiments, the non-polar solvent may be selected from one or more of pentane, petroleum ether, hexanes, n-hexane, heptane, diisopropyl ether, toluene, chloroform, and methylene chloride. In specific embodiments, the non-polar solvent is petroleum ether, pentane, n-hexane, or hexanes.

In some embodiments, the polar solvent may be selected from one or more of diethyl ether, tetrahydrofuran, ethyl acetate, acetone, acetonitrile, isopropanol, ethanol, and methanol. In specific embodiments, the polar solvent is selected from one or more of diethyl ether, ethanol, methanol, or ethyl acetate. In some embodiments, the polar solvent is a mix of from 80-99.9 vol % diethyl ether and 20-0.01 vol % ethanol; a mix of from 90-99 vol % diethyl ether and 10-1 vol % ethanol; or diethyl ether mix of 95% diethyl ether and 5 vol % ethanol. In some embodiments, the polar solvent is diethyl ether. In some embodiments, the polar solvent is ethyl acetate.

In some embodiments, a binary solvent system is employed to elute a normal phase silica gel column using a solvent system selected from petroleum ether/diethyl ether, petroleum ether/diethyl ether mix, hexane/diethyl ether, hexane/diethyl ether mix, or hexane/ethyl acetate. For example, a binary mixture of diethyl ether or a mixture of diethyl ether with ethanol and petroleum ether may be used to elute the column. As used herein, the term “diethyl ether mix” refers to a mixture of 95% diethyl ether and 5% ethanol mixture by volume.

At high altitude, such as in Denver (5280 ft.), it may be desirous to compensate for the decreased atmospheric pressure using low boiling point solvents such as petroleum ether and diethyl ether. For example, the temperature at which the preparative chromatography is performed may be controlled, as well as the pressure, may be controlled to remediate possible discrepancies between “solvent delivered by pump system” and “solvent actually present on column.”

In particular, it was observed that, at temperatures above 70 degrees Fahrenheit and high altitude (5280), the pump “sucks” low boiling solvent into its chamber, and the decreased pressure causes a large amount of solvent to vaporize. This apparently ends up filling the pump and line with air bubbles that inhibit reliable and accurate solvent delivery to the chromatography column. In order to minimize this effect, the chromatography may be performed at temperatures below 70 degrees Fahrenheit when in low atmospheric pressure environments. For example, in some embodiments, the preparative chromatography may be performed at a temperature from about 20 to 70 degrees Fahrenheit, 22 to 65 degrees Fahrenheit, 32 to 60 degrees Fahrenheit, or 40 to 55 degrees Fahrenheit. In some embodiments, the chromatography is performed at a cold room temperature from about 22-42 degrees Fahrenheit.

The second specific problem encountered is when diethyl ether contacts silica, the wetting process is slightly exothermic. On a large scale the heat released by this exothermic reaction is enough to vaporize some of the diethyl ether and petroleum ether. This may lead to unreliable and inaccurate solvent delivery to the chromatography column. In order to address this second issue, the solvent gradients may be changed slightly (i.e. from 5% diethyl ether on a small scale to 7% diethyl ether on a large scale) at high temperature and/or low pressure environments. Additionally, the column may be preconditioned for extra column volumes in order to produce consistent separation over multiple runs on a large scale.

As illustrated, a stopcock 118 is actuated to begin flow of the eluent through the packed column. Other means, such as a mechanical actuator, may be used to control the flow.

The eluent 116 may be flowed through the column in a step-wise fashion. For example, the concentration of diethyl either may be stepped up between the first eluent and the second eluent. In one aspect, for example, a first eluent is 8% diethyl ether mix and 92% petroleum ether (by volume) for 7 column volumes, followed by a second eluent of 30% diethyl ether mix and 70% petroleum ether (by volume) for four column volumes. In another aspect, a first eluent is 4% diethyl ether and 96% petroleum ether (by volume) for 6 column volumes, followed by a second eluent of 8% diethyl ether and 92% petroleum ether (by volume) for four column volumes, followed by a third eluent of 40% diethyl ether and 60% petroleum ether (by volume) for four column volumes. In another aspect, wherein a reverse phase column is employed, the first eluent is 40% H₂O to 60% ethanol (by volume) for 10 CV and the second eluent is 10% H₂O and 90% ethanol (by volume). In other embodiments, a reverse phase column may be eluted used water and one or more of acetonitrile, ethanol, methanol. An acidic modifier such as TFA or formic acid may be added to the water, ethanol, methanol, and/or acetonitrile. It will be appreciated that the flow rate may vary. In some aspects, the flowrate varies based on eluent chosen, the dimensions of the column, and the viscosity of the cannabis oil sample 114. In aspects, where the column volume is 990 mL and the solid phase is silica, the flow rate may be between 100 mL/min and 300 mL/min.

As the extract passes through the column, one through n fractions 118 may be collected, where n is a number representing the number of fractions collected. The n-fractions 118 may be collected at a specific column volume range. For example, one fraction may be collected between 4 and 7 CVs, another fraction may be collected between 8.5 and 9 CVs.

During extraction, liquid chromatography column 102 may be kept at around atmospheric pressure (1 ATM+/−0.2) and around room temperature (22° C.+/−5). FIG. 1 also includes an HPLC-MS 104. In aspects, n-fractions 118 collected using the column 102 may be analyzed. The fractions may first be diluted. For example, a first fraction may be diluted. Additionally or alternatively, the fractions collected may be first concentrated and/or combined with other fractions prior to being analyzed with the HPLC-MS.

FIG. 2 illustrates a liquid chromatographic method 200 for extracting one or more compounds from raw cannabis oil. The one or more compounds may be added to the hemp powder as further described below. Method 200 begins with obtain extract operation 202. In operation 202, raw cannabis oil is extracted from cannabis plant material.

The raw cannabis oil can be obtained by any method known in the art for extraction of Cannabis spp. plant material, or the raw cannabis oil can be purchased from a commercial source. For example, the raw cannabis oil can be obtained by supercritical (or subcritical) CO₂ method that uses carbon dioxide under high pressure and low temperatures to isolate, preserve and maintain the purity of raw cannabis oil. In one specific embodiment, raw cannabis oil obtained from a supercritical CO₂ extraction is used as a starting material for the methods described herein. For example, supercritical CO₂ extraction may be performed as described in U.S. Pat. No. 8,895,078, which is incorporated herein by reference in its entirety. Alternatively, a solvent such as petroleum ether, ethanol, methanol, butanol, acetone, dry ice, or olive oil can be used to extract the Cannabis spp. plant material, at room temperature (ambient temperature) with stirring, by passive extraction, heated to a temperature above room temperature, or under reflux, as known in the art to provide the raw cannabis oil. In another specific embodiment, raw cannabis oil from a butanol extraction is employed as starting material for methods disclosed herein. Any Cannabis spp. plant material can be employed. In some embodiments, the raw cannabis oil is from an extract of Cannabis sativa L. In some embodiments, the cannabis oil is derived from extraction of Cannabis spp. plant material parts selected from one or more of inflorescence of male (staminate) plant, fruiting female (pistillate) plant, staminate flower, stamen, pollen grains, pistillate flower with bract, pistillate flower without bract, seed (archene) with bract, seed without bract, seed without pericarp, leaves, stalks, and roots.

Method 200 then proceeds to prepare column operation 204. In operation 204, a liquid chromatography column is packed. In aspects of the technology, the column described with reference to FIG. 1 is used. It will be appreciated that the column will be packed to compliment the eluent liquid. That is, when a hydrophobic eluent is chosen, the column will be packed with a hydrophilic material, and vice-versa. In aspects, the column is packed with a hydrophilic stationary phase material, such as silica for a normal phase liquid chromatography extraction. Alternatively, a column may be packed with a hydrophobic stationary phase material, such as a carbon 18, phenyl, C4, or C8 reverse phase material.

The column eluate flow is monitored by any known means in the art. In some aspects, the eluate flow is monitored by ultraviolet (UV) absorption, refractive index, thin layer chromatography (TLC), mass spectrometry (MS) total ion detection, or MS mass selective detection. In a particular embodiment, the eluates are monitored by UV and/or mass selective detection. In specific embodiments, the column eluates are monitored by mass selective detection for m/z of one or more of delta-9 tetrahydrocannabinol (THC), tetrahydrocannabinol acid (THCA), cannabidiol (CBD), cannabidiolic acid (CBDA), Cannabigerol (CBG), Cannabichromene (CBC), Cannabinol (CBN), Cannabicyclol (CBL), Cannabivarin (CBV), Tetrahydrocannabivarin (TCHV), Cannabidivarin (CBDV), Cannabichromevarin (CBCV), Cannabigerovarin (CBGV), and Cannabigerol Monomethyl Ether (CBGM). In a specific aspect, eluate is monitored at 315.2 m/z and 345.2 m/z. Monitoring at 315.2 (M+1) will detect CBD and THC, as well as CBC. Monitoring at 345.2 m/z will detect certain other cannabinoid components, for example certain carboxylic acid containing cannabinoid compounds. Unless otherwise specified, percent values refer to weight percent.

Method 200 then proceeds to insert cannabis oil sample operation 208. In aspects, the raw cannabis oil extracted at operation 202 is injected into the column. In other aspects, the raw cannabis oil is first diluted as described above. In a particular embodiment, a column volume of 0.05 CVs of cannabis oil sample may be injected into the column.

Method 200 then proceeds to stage one elution operation 206. In operation 206, a first eluent is added to the column. In aspects, the first eluent is 8% diethyl ether mix and 92% petroleum ether (by volume), 4% diethyl ether and 96% petroleum ether (by volume), or 40% H₂O to 60% ethanol (by volume).

Method 200 then proceeds to collect stage one fractions operation 207. Where the first eluent is 8% diethyl ether mix and 92% petroleum ether (by volume) the first fraction may be collected between 0 and 4 CVs. Where the first eluent 4% diethyl ether and 96% petroleum ether (by volume), the first fraction may be collected between 0 and 2 CVs, and the second fraction may be collected between 2 and 6 CVs. Further, where the first eluent is 40% H₂O to 60% ethanol (by volume), the first fraction may be collected between 0 and 4 CVs, and the second fraction may be collected between 4 and 7 CVs. These and other fractions may be collected and added to form a hemp powder as described above.

Method 200 then proceeds to stage two elution operation 208. In operation 208, a second eluent is added to the column. In one aspect, a second eluent is 30% diethyl ether mix and 70% petroleum ether (by volume), 8% diethyl ether mix and 92% petroleum ether (by volume), or second eluent is 10% H₂O and 90% ethanol (by volume).

Method 200 then proceeds to collect stage two fractions operation 209. Where the second eluent is 30% diethyl ether mix and 70% petroleum ether (by volume) the second fraction may be collected between 4 and 8 CVs, the third fraction may be collected between 8.5 and 9 CVs, the fourth fraction may be collected between 9 and 9.5 CVs the fourth fraction may be collected between 9.5 and 10 CVs, and the fifth fraction may be collected between 10 and 13 CVs. Where the first eluent 8% diethyl ether and 92% petroleum ether (by volume), the third fraction may be collected between 7 and 9.5 CVs. Further, where the first eluent is 10% H₂O to 90% ethanol (by mass), the first fraction may be collected between 7 and 9 CVs the fourth fraction may be collected between 9 and 12 CVs. These and other factions may be collected and used to form the hemp powder as further described below.

Method 200 optionally proceeds to stage three elution operation 210. In operation 210, a third eluent is added to the column. In aspects of the technology, a third eluent of 40% diethyl ether and 60% petroleum ether (by volume) is added.

Method 200 then optionally proceeds to collect stage three fractions operation 211. Where the third eluent of 40% diethyl ether and 60% petroleum ether (by volume), the fourth fraction may be collected between 9.5 and 14 CVs. These and other factions may be collected and used to form the hemp powder as further described below.

FIG. 3 illustrates a method 300 for concentrating one or more fractions. These concentrations may be used to form the hemp powder as further described below. Method 300 begins with combine fractions operation 302. In some embodiments, the normal phase column first eluent is 8% diethyl ether mix in 92% petroleum ether and is run at a rate of 200 mL/min. After 4 CV (3960 mL where the column volume is 990 mL), a second eluent of 30% diethyl ether mix and 70% petroleum ether (by volume) may then be added to the column. In aspects, 120 ml fractions are collected. In one embodiment, eluate from 1-4 CV and 9-20 CV are collected, pooled, evaporated and combined to provide a clean cannabis oil having 60-70% CBD and not more than 0.3% THC. Additionally, fractions 4-8 may be separately combined, evaporated, and optionally recrystallized to provide a CBD isolate from any appropriate solvent, e.g., n-hexane, or pentane.

Operation then proceeds to evaporate eluent operation 304. In evaporate eluent operation, the eluent is evaporated from the extract. In some embodiments, the eluent is removed in vacuo. In aspects, the combined fractions described above with reference to operation 302 are exposed to an environment of 0.3 ATMs, a temperature of 45 degrees Celsius, and agitated. In other aspects, each fraction is concentrated prior to combination. Operation 304 may continue until one or more compounds precipitates from the combined liquid fraction.

FIGS. 4-9 illustrate various analytical HPLC-MS chromatograms that were generated using aspects of the technology disclosed herein. To generate each chromatogram, a single-quad MS detector rather was used. The total ion chromatogram as well as two specific masses: 315.2 amu and 345.2 amu were monitored.

FIG. 4 is illustrates analytical HPLC-MS chromatograms 401 and 403, of standards of a combined CBD and THC monitored at m/z 315.2 (M+H). The samples of the CBD and THC were obtained as commercial standards (Sigma-Aldrich). Illustrated in the chromatogram 401 is CBD peak 402 and THC peak 404. As illustrated in chromatogram 401, the CBD peak 402 has a retention time of about 1.3 min, and the THC peak 404 has a retention time of about 2.4 minutes. Further, illustrated in chromatogram 403 monitored at m/z 345.2, shows certain very minor cannabinoid components eluting at peaks 406 (with a retention time of around 0.4 minutes) and 408 (with a retention time of around 1.1 minutes).

FIG. 5 is an HPLC-MS chromatogram 500 of crude cannabis oil. The crude oil of this sample was prepared using a supercritical CO₂ extraction method. The sample was prepared by mixing raw cannabis oil with a diluting solvent. As illustrated, FIG. 5 includes two HPLC-MS chromatograms, namely, a first chromatogram 501 monitored at m/z 315.2 and a second chromatogram 503 monitored at m/z 345.2. The first chromatogram 501 illustrates a peak 502 at around 1.3 mins retention time. By comparing the peak 502 to the CBD peak 402 illustrated in FIG. 4, it will be appreciated that peak 502 illustrates the CBD peak. The amount 510 of peak 502 is 64%. Additionally illustrated in chromatogram 501 are other minor peaks 504. Other peaks 504 represent various other compounds present in the bulk cannabis oil.

Second chromatogram 503 illustrates peak 506, at m/z 345.2 (M+H). Additionally illustrated in second chromatogram 503 is other peaks 508, which represents other compounds contained in the raw cannabis sample.

FIG. 6 illustrates HPLC-MS chromatograms 601 and 603 of raw cannabis oil. The raw cannabis oil is same starting material as the raw cannabis oil referenced with respect to FIG. 5, but the raw cannabis oil has been diluted. As illustrated, FIG. 6 includes two HPLC-MS Chromatograms, a first chromatogram 601 and a second chromatogram 603. The first chromatogram 601 illustrates a peak 602 at around 1.3 mins retention time. By comparing the peak 602 to the CBD peak 402 illustrated in FIG. 4, it will be appreciated that peak 602 illustrates a CBD peak. Additionally illustrated in chromatogram 601 is other peaks 604. Other peaks 604 represent various other compounds present in the bulk cannabis oil. The amount 610 of peak 602 is around 65%.

Second chromatogram 603 illustrates peak 606 at m/z 345.2 (M+H). Additionally illustrated in second chromatogram 603 are other peaks 608, which represents other compounds contained in the raw cannabis sample.

As illustrated, FIG. 7 includes two HPLC-MS Chromatograms of the clean cannabis oil obtained in Example 1, namely, a first chromatogram 701 and a second chromatogram 703. The first graph 701 illustrates a peak 702 at around 1.3 mins retention time. By comparing the peak 702 to the CBD peak 402 illustrated in FIG. 4, it will be appreciated that peak 702 illustrates a CBD peak. Additionally chromatogram 701 includes other peaks 704. Other peaks 704 represent various other compounds present in the clean sample oil. The amount 710 of peak 702 is around 68%.

Second chromatogram 703 illustrates peak 706 at m/z 345.2 (M+H). Additionally illustrated in second chromatogram 703 is other peaks 708, which represents other compounds contained in the raw cannabis sample.

FIG. 8 illustrates HPLC-MS chromatograms for a combined and diluted sample of clean cannabis oil of Example 1. The cannabis oil sample was the same as the cannabis oil sample referenced with respect to FIG. 7, but has been further diluted. Dilution occurred by addition of a solvent prior to analytical HPLC. As illustrated, FIG. 8 includes two HPLC-MS Chromatograms, namely, a first chromatogram 801 and a second chromatogram 803. The first chromatogram 801 illustrates a peak 802 at around 1.3 mins retention time. Comparing the peak 802 to the CBD peak 402 illustrated in FIG. 4, it will be appreciated that peak 802 illustrates the CBD peak. Additionally, chromatogram 801 includes other peaks 804. Other peaks 804 represent various other compounds present in the bulk cannabis oil. The area 810 of peak 802 is around 69%.

Second chromatogram 803 illustrates peak 806 at m/z 345.2 (M+H). Additionally illustrated in second chromatogram 603 are other peaks 608, which represents other compounds contained in the cannabis oil sample.

As illustrated, FIG. 9 includes two HPLC-MS chromatograms, a first chromatogram 901 and a second chromatogram 903. The first chromatogram 901 illustrates a peak 902 at around 1.3 mins retention time. By comparing the peak 902 to the CBD peak 402 illustrated in FIG. 4, it will be appreciated that peak 902 illustrates the CBD peak. Additionally, chromatogram 901 includes other peaks 904. Other peaks 904 represent various other compounds present in the cannabis oil sample. The area 910 of peak 902 is around 95.1%.

Second chromatogram 903 illustrates minor peak 906 at m/z 345.2 (M+H). Additionally illustrated in second chromatogram 903 are other minor peaks 908, which represents other compounds contained in the cannabis oil sample.

Example 1. Normal Phase Preparative Method 1

In this example, a Biotage Isolera Flash Chromatography System was employed to process raw cannabis oil to deplete THC component to provide clean cannabis oil, and further to provide CBD isolate. HPLC purity of starting crude cannabis oil used herein was 60.50% CBD and 3.50% THC.

45 g hemp oil (injection mass 6 wt %) was dissolved in 22.5 mL petroleum ether and injected to a 750 g normal phase silica gel column (SNAP KP-Sil 750 g, BIOTAGE) and rinsed with pet ether for a total injection volume of 67.5 mL. Solvent A was petroleum ether; Solvent B was 95% diethyl ether and 5% ethanol. Solvents A and B were employed to elute the column in a step gradient of 8 vol % B run for 7 column volumes, increased from 8-30 vol % B for 0 column volume, then 30 vol % B for 6 column volumes at a flow rate of 200 mL/min. The column eluate was monitored by UV-vis at 220 nm, and 240 nm, as shown in FIG. 10. 120 mL fractions were collected. Following elution, the peak fractions were subjected to analytical HPLC or TLC analysis. Appropriate fractions were combined and solvents removed by rotoevaporation. Analytical HPLC by the method of Example 4 was employed to determine relative amounts of cannabinoids of interest.

As shown in FIG. 10, all eluate before 4 CV, fractions 1-20, (˜1-6 CV) and all eluate from 9-12 CV were pooled and concentrated to make isolate 1. Following evaporation of solvents from isolate 1, clean oil was obtained in about a 70 wt % crude yield. This is a result of conservative fraction collection and the loss of THC and minor portions of contaminated CBC. HPLC purity of clean cannabis oil was 69% CBD and <0.3% THC as shown in FIGS. 7 and 8.

Fractions 21-30 were collected, pooled and concentrated to make isolate 2. Isolate 2 was about 25 wt % of the starting material. Isolate 2 was either sold as is, recrystallized to further purify, or added back to clean oil in about a 1:2 ratio to increase the yield of clean oil to 90-95% from starting crude. HPLC purity of purified isolate is 95% CBD and <0.3% THC, as shown in FIG. 9.

Example 2. Normal Phase Preparative Method 2

In this example, a Biotage Isolera Flash Chromatography System was employed to process raw cannabis oil to deplete THC component. In particular, 45 g hemp oil (injection mass 6 wt %) was dissolved in 22.5 mL petroleum ether and injected to a 750 g normal phase silica gel column (SNAP KP-Sil 750 g, BIOTAGE) and rinsed with pet ether for a total injection volume of 67.5 mL. Solvent A was petroleum ether; Solvent B was 99.9% diethyl ether. Solvents A and B were employed to elute the column at 200 mL/min in a step gradient of 4 vol % B for 6 column volumes, then 8 vol % B for 4 column volumes, then 40 vol % B for 4 column volumes. Eluate was monitored at 220 nm and 240 nm. 120 mL fractions were collected. Following elution, the peak fractions were subjected to analytical HPLC or TLC analysis. Fractions 1-20 (1-6 CV) and 36-45 (11.5-14 CV) were combined and solvents removed by rotoevaporation. Analytical HPLC was employed to determine relative amounts of cannabinoids of interest.

Example 3. Reverse Phase Preparative Method 3

In this example, a Biotage Isolera Chromatography System was employed using a preparative Reverse Phase C18 column to process raw cannabis oil. 8.0 g hemp oil (injection mass 2 wt %) was dissolved in 16 mL ethanol and injected to a 400 g RP C18 column (SNAP C18 400 g) and rinsed with ethanol for a total injection volume of 24 mL. Solvent A was water; Solvent B was ethanol. Solvents A and B were employed to elute the column at 100 mL/min in a gradient of 60-90 vol % B (ethanol/formic acid) over 10 column volumes. Column eluate was monitored at 220 nm, and 100 mL fractions were collected. Following elution, the peak fractions were subjected to analytical HPLC or TLC analysis. Appropriate fractions were combined and solvents removed by rotoevaporation. Analytical HPLC was employed to determine relative amounts of cannabinoids of interest.

Example 4. Reverse Phase Analytical HPLC Method

Raw cannabis oil and process samples were evaluated by HPLC, or HPLC-MS by diluting sample at 60 uL/6 mL with an injection volume of 1 uL. Solvent A is water 0.1% formic acid; Solvent B is acetonitrile 0.1% formic acid. The C18 analytical column (Agilent Eclipse Plus C-18/RRHD 1.8 um 21×50 mm) is run at 50° C., at 0.5 mL/mn in a gradient elution of 70% B from 0-3 minutes, then 70-95% B from 3-5 min. HPLC-MS employed dual ion monitoring using ES-API, positive ion monitoring at 315.2 amu (Signal 1, MSD1) and 345.2 amu (Signal 2, MSD2). FIGS. 4-9 illustrate various analytical HPLC-MS chromatograms. To generate each chromatogram, a single-quad MS detector rather was used. The total ion chromatogram as well as two specific masses: 315.2 amu and 345.2 amu. Calibration curves developed from external reference standards for Cannabidiol (CBD) (Sigma-Aldrich), and d9-THC (Sigma-Aldrich). Using this method, HPLC purity of crude cannabis oil used herein was 60.50% CBD and 3.50% THC. HPLC purity of purified clean cannabis oil from Method 1 was 69% CBD and <0.3% THC. HPLC purity of purified isolate from Method 1 was 95% CBD and <0.3% THC, as discussed in Example 1.

Example 5. Production Normal Phase CBD Isolate Method

The following protocol of Example 5 has been used:

Preparation:

1. Dissolve 750 g of crude oil in 400 mL of petro ether. Use “gentle” heating and cap with foil with a large stir bar. Record sensory characteristics of starting material description (color, consistency, smell, etc.) and record actual mass of starting material (g).

2. Once everything is dissolved, let crude oil mixture cool to room temperature and make sure everything is liquid. There should be about 1200 mL of total mixture in the syringes. Record the total volume of mixture prior to injection (mL) and the description of injection material (color, consistency).

3. Prepare 3 gradient tanks:a.G1: 6% ethyl ether in petroleum ether (3.6 L of ethyl ether in 56.4 L of petroleum ether); b.G2: 15% ethyl ether in petroleum ether (9 L of ethyl ether in 51 L of petroleum ether); and c.G3: 80% ethyl ether in petroleum ether (48 L of ethyl ether in 12 L of petroleum ether).

4. Turn on column compression and set to ˜100 PSI.

5. Run G1 for 1.5 CV (13 L) to condition the 5 kg column. Collect the solvent from this run in a “recycle” solvent container. Solvent pressure should be between 30-35 PSI and flowing at ˜1 L per minute.

6. Load sample. Increase pressure to ˜80 PSI to load sample faster. Record Load time (min).

7. Decrease solvent pressure back to 30-35 PSI. Begin running G1 solvent again.

Collection:

8. Initial collection: a.Collect 1 CV (9 L) of solvent in a 10 L carboy labelled A. (If yellow color is observed before 9 L switch solvent line to a new carboy immediately.) Record volume of solvent before yellow observed (L); b.Collect an additional 0.5 CV (4 L) in a 10 L carboy labelled B.

9. Fraction collection: Notes: All fractions are 6 L. Collect all fractions in 10 L carboys.

a. Collect 1 CV (1 fraction). (6 L).

b. After Fraction 1 stop solvent flow and switch to G2 ISO.

c. Continue collecting fractions.

d. After Fraction 7 stop solvent flow and switch to G3.

e. Collect Fractions 8, 9, and 10. (If solvent is still colored yellow after fraction 10 collect additional fractions.)

Analysis:

10. Run TLC on fractions to determine CBD containing fractions for crystallization, disposal, and recombination. Collected and record each of isolate fractions, raffinate fractions, THC disposal fractions, collected cannabinoid fractions. Record description of isolated fractions (approx. volume, color). Record description of raffinate fractions (approx. volume, color).

Raffinate Concentration:

11. Collect raffinate fractions in a preweighed 20 L flask. Concentrate raffinate fractions under reduced pressure. Set vacuum to 0 mtorr and bath to 55° C. Keep this raffinate for future use. Record Mass of flask (g). Record Description of concentrated raffinate oil (color, consistency). Mass of raffinate oil (g).

Cannabinoid Concentration:

12. Collect cannabinoid fractions in a preweighed 20 L flask. Concentrate cannabinoid fractions under reduced pressure. Set vacuum to 0 mtorr and bath to 65° C. Keep these cannabinoids for future use. Record mass of flask (g), description of concentrated cannabinoids (color, consistency), and mass of cannabinoid oil (g).

Crystallization:

13. Tare a 5 L round bottom flask. Concentrate isolate fractions under reduced pressure. Set vacuum to 0 mtorr and bath to 65° C. Record Mass of flask (g), and mass of isolate R1 (g).

14. Dissolve isolate R1 in 2×(mass of isolate R1) in mL of hot hexanes. Record volume of hot hexanes used (mL).

15. Seed crystallization dish with enough crystals to sparsely cover the bottom of the container. Cover crystallization dish with foil and place in freezer at 30° F. for 12 h.

16. Decant crystallization dish and rinse crystals with cold hexanes. The decanted solution and rinse hexanes should be collected and labelled “mother liquor”. Collect and mass rinsed crystals that remain in the tray. These crystals will be labelled isolate R2. Record Description of mother liquor/rinse combination (color). Description of isolate R2 (color, consistency). Mass of isolate R2 (g).

17. Dissolve isolate R2 in ˜2×(mass of isolate R2) in mL of hot hexanes.

18. Seed crystallization dish with enough crystals to sparsely cover the bottom of the container. Cover with foil and let crystallize for 12 h at room temperature. Record room temperature (° F.).

19. Decant new mother liquor and rinse crystals with cold petroleum ether. This rinse and decanted material should be combined with “mother liquor” from Step 16.

20. Collect the crystals remaining in tray and crush using mortar and pestle. Labelled this material isolate F. Mass isolate F right after grinding. Record Description of final crystals (color, consistency). Record Mass of isolate F post grinding (g).

21. Dry isolate F under reduced pressure or in a vacuum oven at 50° C. Record Description of isolate F (color, consistency). Record Mass of isolate F post drying (g).

Example 6. Production THC Removal Method

The following protocol of Example 6 has been used:

Preparation:

1. Dissolve 500 g of crude oil in 250 mL of petro ether. Use “gentle” heating and cap with foil with a large stir bar. Record Starting material description (color, consistency, smell, etc.). Record Mass of starting material (g).

2. Once everything is dissolved, let crude oil mixture cool to room temperature and make sure everything is liquid. There should be about 750 mL of total mixture in the syringes. Record Total volume of mixture prior to injection (mL). Record Description of injection material (color, consistency).

3. Prepare 3 gradient tanks:

a.G1: 6% ethyl ether in petroleum ether (3.6 L of ethyl ether in 56.4 L of petroleum ether);

b.G2: 12% ethyl ether in petroleum ether (7.2 L of ethyl ether in 52.8 L of petroleum ether); and

c.G3: 80% ethyl ether in petroleum ether (48 L of ethyl ether in 12 L of petroleum ether).

4. Turn on column compression and set to ˜100 PSI.

5. Run G1 for 1.5 CV (13 L) to condition the 5 kg column. Collect the solvent from this run in a “recycle” solvent container. Solvent pressure should be between 30-35 PSI and flowing at ˜1 L per minute.

6. Load sample. Increase pressure to ˜80 PSI to load sample faster. Record Load time (min).

7. Decrease solvent pressure back to 30-35 PSI. Begin running G1 solvent again.

Collection:

8. Initial collection: d.Collect 1 CV (9 L) of solvent in a 10 L carboy labelled A. (If yellow color is observed before 9 L switch solvent line to a new carboy immediately.) Record volume of solvent before yellow observed (L).e.Collect an additional 1 CV (9 L) in a 10 L carboy labelled B.

9. Fraction collection:

f. Collect 4 CV (36 L) in 2 L fractions. (18 fractions).

g. After Fraction 18 stop solvent flow and switch to G2.

h. Continue collecting Fractions in 2 L portions.

i. After fraction 31 stop solvent flow and switch to G3.

10. Final Fraction Collection:

j. After Fraction 36 switch collection to 10 L carboys.

k. Collect two 8 L fractions labelled X and Y. (If solvent is still colored yellow after fraction Y collect an additional 8 L fraction labelled Z.)

Analysis:

11. Run TLC on fractions to determine CBD containing fractions for crystallization, disposal, and recombination. Record Collected isolate fraction number. Record Collected raffinate fraction numbers. Record Collected disposal fraction numbers. Record Description of isolation fractions (approx. volume, color). Record Description of raffinate fractions (approx. volume, color).

Raffinate Concentration:

12. Collect raffinate fractions in a preweighed 20 L flask. Concentrate raffinate fractions under reduced pressure. Set vacuum to 0 mtorr and bath to 55° C. Record Mass of flask (g). Record Description of concentrated raffinate oil (color, consistency). Record Mass of raffinate oil (g).

Crystallization:

13. Tare a 5 L round bottom flask. Concentrate isolate fractions under reduced pressure. Set vacuum to 0 mtorr and bath to 65° C.Record Mass of flask (g).Record Mass of isolate R1 (g).

14. Dissolve isolate R1 in 2×(mass of isolate R1) in mL of hot hexanes.Record Volume of hot hexanes used (mL).

15. Seed crystallization dish with enough crystals to sparsely cover the bottom of the container. Cover crystallization dish with foil and place in freezer at 30° F. for 12 h.

16. Decant crystallization dish and rinse crystals with cold hexanes. The decanted solution and rinse hexanes should be collected and labelled “mother liquor”. Collect and mass rinsed crystals that remain in the tray. These crystals will be labelled isolate R2. Record Description of mother liquor/rinse combination (color).Record Description of isolate R2 (color, consistency). Record Mass of isolate R2 (g).

17. Dissolve isolate R2 in ˜2×(mass of isolate R2) in mL of hot hexanes.

18. Seed crystallization dish with enough crystals to sparsely cover the bottom of the container. Cover with foil and let crystallize for 12 h at room temperature. Record Room temperature (° F.).

19. Decant new mother liquor and rinse crystals with cold petroleum ether. This rinse and decanted material should be combined with “mother liquor” from Step 16.

20. Collect the crystals remaining in tray and crush using mortar and pestle. Labelled this material isolate F. Mass isolate F right after grinding. Record Description of final crystals (color, consistency).Record Mass of isolate F post grinding (g).

21. Dry isolate F under reduced pressure or in a vacuum oven at 50° C. Record Description of isolate F (color, consistency). Record Mass of isolate F post drying (g).

Formulation

22. Dissolve isolate F in 2×(mass of isolate F) in mL of petroleum ether. Add this mixture to the flask containing raffinate oil. Stir combined mixture at 55° C. for 20 minutes.

23. Concentrate final oil under reduced pressure. Set vacuum to 0 mtorr and bath to 55° C. Record Mass of flask (g); (should be the same as Step 12). Record Description of final oil (color, consistency. Record Mass of final oil (g).

Example 7. Pre-Process. Concentration of CBD

The following protocol of Example 7 has been used:

1. Add 1000 mL of warm crude oil (55° C.) to a 3000 mL beaker. Record mass (g).

2. Add 500 mL of petroleum ether to the warm crude oil. Stir under gentle heat until the crude oil is dissolved to obtain a homogenous mixture. Use a stir rod and magnetic stirring. Do not heat mixture over 35° C.

3. Let the mixture cool to room temperature over 15 minutes.

4. Place the mixture into an ice bath and cool to 0° C. for 15-60 minutes. Use auto stirrer with a large blade and stir on the lowest speed setting.

5. Add approximately 500 mL of cold petroleum ether to the solid mixture and use the auto stirrer with the small blade to re-blend the mixture. Blend until homogeneous. Note: samples can then be placed into the freezer and left overnight instead of step 6. Placing the samples in the freezer provides slightly better yield (e.g., 5-10% greater).

6. Place the mixture into an ice bath and cool at 0° C. for 60 minutes. Stir by hand with a large metal spatulaevery 15 minutes, or with an overhead stirrer constantly to homogenize. Alternatively, simply let the mixture cool in an ice bath at 0° C. for 60 minutes.

7. Add approximately 1 L of cold petroleum ether to the filter to prime the filter.

8. Add 0.5 L of cold petroleum ether to the beaker with the mixture. Mix gently in the beaker. Pour the mixture into the filter and stir gently. It should be a light orange/yellow and look like a smoothie. Break up any clumps at this point by pressing them against the side of the filter with the spatula.

9. Place the filter under vacuum. Mix with a large spatula until clumpy light yellow solid remains. It should be a cookie dough like consistency.

10. Remove filter from vacuum. Close the vacuum valve. Add approximately 0.75 L of cold petroleum ether to the filter and stir with a large spatula until the solid is homogenously mixed. It should look like a vanilla milkshake.

11. Place the filter under vacuum. Mix with a large spatula until white remains. It should be a powder like consistency.

12. Remove filter from vacuum. Close the vacuum valve. Add approximately 0.75 L of cold petroleum ether to the filter and stir with large spatula until the solid is homogeneously mixed. It should look like a vanilla milkshake.

13. Place the filter under vacuum. Mix with a large spatula until white remains. It should be a powder like consistency.

14. Using a scoopula or spatula, scrape all the white powder off of the filter into a tared foil tin. Place into vacuum oven at 50° C. and place under vacuum for one hour.

15. Collect the filtrate and concentrate in a 20 L flask for later use.

Example 8. Production THC Removal Method

The following protocol of Example 8 has been used:

Preparation:

1. Pour 10×20 L bottles of diethyl ether into a 55 gallon drum. Seal the lid on this drum tightly.

2. Prepare four gradient tanks:

a. Prep Tank (PT): 100% petroleum ether (15.9 Gal (60 L) of petroleum ether)

b. Gradient 1 (G1): 6% diethyl ether in petroleum ether (1.0 Gal (3.6 L) of diethyl ether in 14.9 Gal (56.4 L) of petroleum ether)

c. Gradient 2 (G2): 15% diethyl ether in petroleum ether (2.4 Gal (9 L) of diethyl ether in 13.5 Gal (51 L) of petroleum ether)

d. Gradient 3 (G3): 80% diethyl ether in petroleum ether (12.7 Gal (48.0 L) of diethyl ether in 3.2 Gal (12.0 L) of petroleum ether)

3. Insert 5 kg Flash 150 silica column into the steel Flash 150 pressure vessel. Gently tap the column with a rubber hammer to ensure it sits flush with the bottom of the pressure vessel. Close the lid and tightly seal the pressure vessel lid.

4. Ensure all the pressure valves on the entire Flash 150 system are in the closed position.

5. Connect the Flash 150 manifold to the house air. Ensure the house air pressure is no greater than 120 psi using the regulator.

6. Connect the column compression line to the Flash 150 column compression inlet. Turn on column compression and set to 100 psi. Ensure the red pressure indicator is sticking out of the edge of the Flash 150.

7. Connect solvent pressure line A to gradient tank PT via the quick connect pressure inlet. Connect solvent pressure line B to the sample loading chamber via the quick connect pressure inlet. Connect the column inlet line to the solvent outlet valve on the gradient tank PT.

8. Turn on pressure to solvent line A and use the regulator to set the solvent line pressure at approximately 60 psi. Open the solvent outlet valve on gradient tank PT.

9. Turn column inlet so the valve arrow faces solvent line PT. This will enable solvent to flow through the column. (Note: If the column has never been used before, it may take a few minutes for solvent to start flowing from the column outlet valve.)

10. Run gradient tank PT for 17 L (2 CV) to condition the column. Collect all the solvent from this run in a “recycle” solvent container. Solvent should flow out of the column at approximately 2 L per minute. After 17 L of solvent are collected, turn the solvent inlet to the off position. Turn the solvent outlet valve on the gradient tank PT to the off position.

11. Turn the solvent pressure to line A off. Disconnect line A from gradient tank PT and connect line A to gradient tank G1 via the quick connect pressure inlet.

12. Turn the column solvent inlet valve so the valve arrow faces the sample loading vessel line. Increase system pressure to approximately 80 psi. Turn on pressure to solvent line B. Turn on the pressure inlet valve of the sample loading vessel.

13. The sample will begin loading. Watch the sample travel through the clear sample loading tube into the column. Immediately after the entire sample has been loaded onto the column, turn the solvent inlet valve on the column to the off position.

14. Turn off the pressure inlet valve on the sample loading vessel. Decrease the system pressure to 20-30 psi. Disconnect solvent pressure line B from the sample loading vessel and connect solvent pressure line B to gradient tank G2 via the quick connect pressure inlet.

Collection:

15. Gradient Tank 1 (2×10 L fractions, 11×2 L fractions (fractions 1-11)):

a. Ensure the column outlet tube is placed in a 10 L jug labelled Pre1.

b. Turn on solvent pressure line A connected to G1. Ensure the pressure is at 30 psi. open the solvent outlet valve on gradient tank G1. Turn column inlet so the valve arrow faces solvent line G1. Solvent will begin flowing through the column.

c. Collect 10 L (1 CV) of solvent in a 10 L jug A.

d. Collect an additional 10 L (1 CV) in a 10 L jug labelled Pre2. Note: If tallow color is observed before 9 L immediately switch the column outlet tube to 10 L jug B.

e. Begin collecting 2 L fractions in fraction vessels (11 total fractions).

f. After fraction 11, place the column outlet tube in fraction vessel 12 and immediately turn off the column inlet valve connected to solvent line G1. Turn off the solvent outlet valve on gradient tank G1. Turn off solvent pressure line A.

16. Gradient Tank 2 (5×2 L fractions (fractions 12-16)):

a. Turn on solvent pressure line B connected to G2. Ensure the pressure is at 30 psi. Open the solvent outlet valve on gradient tank G2. Turn column inlet so the valve arrow faces solvent line G2.

b. Continue collecting fractions in 2 L portions (5 total fractions).

c. While fractions are being collected, disconnect solvent pressure line A from gradient tank G1 and connect solvent pressure line A to gradient tank G3 via the quick connect pressure inlet.

d. After fraction 16, place the column outlet tube in fraction vessel 17 and immediately turn off the column inlet valve connected to solvent line G2. Turn off the solvent outlet valve on gradient tank G2. Turn off solvent pressure line B.

17. Gradient Tank 3 (4×2 L fractions (fractions 17-20), 2×10 L fractions):

a. Turn on solvent pressure line A connected to G3. Ensure the pressure is at 30 psi. Open the solvent outlet valve on gradient tank G3. Turn column inlet so the valve arrow faces solvent line G3.

b. Continue collecting fractions in 2 L portions (4 total fractions).

c. After fraction 30 switch collection to 10 L jugs.

d. Collect one 10 L fraction labelled Post1. (If solvent is still colored yellow after fraction Post1 collect an additional 8 L fraction labelled Post2.)

e. After fraction Post2/3 turn off the column inlet valve connected to solvent line G3. Turn off the solvent outlet valve on gradient tank G3. Turn off solvent pressure line A.

f. Solvent may continue flowing. Continue collecting solvent in a recycle container until solvent is no longer flowing.

18. Ensure all pressure valves on the system are closed.

19. Ensure connection to house air is closed.

20. Ensure all solvent tanks and the Flash 150 column are completely vented.

21. Clean the sample loading vessel thoroughly with petroleum ether.

Analysis:

22. Run TLC on fractions to determine CBD containing fractions for crystallization, disposal, and recombination.

Raffinate Concentration:

23. Collect raffinate fractions in a tared 20 L flask. Concentrate raffinate fractions under reduced pressure. Set vacuum to 0 mtorr and bath to 55° C. Analyze final dried raffinate with LCMS to determine CBD and THC content.

Crystallization:

24. Tare the 20 L round bottom flask. Label with Date/Batch Number/Initial Tare. Record initial flask tare (g). Record final flask tare (g). Record mass of isolate oil (g).

25. Take the mass of the isolate oil and multiply by 2. The production of this multiplication is the amount of n-hexane that should be added to the 20 L round bottom flask. Record volume of n-hexane (mL).

26. Place the round bottom flask on the rotor at 55 rpm in a hot water bath at 35° C. Do not place under vacuum. Allow to rotate until all of the isolate oil is dissolved and the mixture is homogeneous.

27. Pour the isolate oil mixture into pyrex trays. Each tray should be filled appropriately 0.5 to 1 inches high. Immediately after pouring cover trays with aluminum foil to prevent solvent evaporation.

28. Let the trays cool to room temperature and then lightly seed with isolate crystals. Recover with aluminum foil.

29. Place trays in freezer at −6° C. for approximately 8-10 hours.

30. A layer of crude crystals should have developed. Decant the orange-yellow hexane layer into mother liquor drum.

31. Rinse the crude crystals with approximately 50-100 mL of cold petroleum ether and decant into mother liquor drum.

32. Repeat the rinse.

33. Let the crystals dry at room temperature in fume hood for 1 hour.

34. Crush up the crystals and obtain a mass. Record mass of cyrstals R1 (g).

Second Crystallization:

35. Take the mass of crystals R1 and multiply by 2. The product of this multiplication is the amount of n-hexane that should be added to the 20 L Erlenmeyer flask. Cover the flask lid with a piece of foil to prevent evaporation. Record volume of n-hexane (mL).

36. Stir the n-hexane at 35° C. with a magnetic stir rod until the solvent comes to a boil.

37. Add the crystals from R1 to the hot stirring n-hexane. Stir at 35° C. with a magnetic stir rod until the solvent comes to a boil.

38. Add the crystals from R1 to the hot stirring n-hexane. Stir at 35° C. until the solid is dissolved.

39. Pour the crystallized mixture into pyrex trays. Each tray should be filled approximately 0.5 to 1 inches high. Immediately after pouring cover trays with aluminum foil to prevent solvent evaporation.

40. Let the trays sit at room temperature undisturbed for 8-10 hours.

41. A layer of pristine should have developed. Decant the light-yellow hexane layer into mother liquor drum.

42. Rinse the crude crystals with approximately 50-100 mL of cold petroleum ether and decant into mother liquor drum.

43. Repeat the rinse.

44. Let the crystals dry at room temperature in fume hood for 1 hour. Then break up crystals and transfer to grinder.

45. Grind crystals into a fine powder and transfer to aluminum trays. The powder should completely coat the bottom of the aluminum trays, but the powder layer should be no greater than 0.5 inches.

46. Place the aluminum trays with powder into the vacuum over at 35° C. and place under vacuum for one hour.

Record mass of final crystals (from crystals R1) (g). Record mass of final crystals (from pre-run isolate) (g).

Formulation:

47. Dissolve specific amount of CBD isolate in 2×(mass of CBD isolate) in mL of petroleum ether. Add this mixture to the flask containing raffinate oil. Stir combined mixture at 35° C. for 20 minutes.

48. Concentrate final oil under reduced pressure. Set vacuum to 0 mtorr and bath to 35° C. Record mass of flask (g). Record description of final oil (color, consistency). Record mass of final oil (g).

Example 9. Post-Processing. CBG and CBC Isolation

The following protocol of Example 9 has been used:

1. Concentrate the cannabinoids fraction obtained upon column chromatography of the filtrate oil in Example 8 under reduced pressure.

2. Obtain a mass of the cannabinoids oil. For every gram of oil, add 1 mL of hot ethanol.

3. Stir the hot ethanol and cannabinoids oil until a homogeneous mixture is obtained (concentration=0.33 g/mL).

4. Attach a 400 g reverse phase column to the Biotage Isolera. Equilabrate for 3 CV with 80% methanol and 20% distilled water.

5. Inject 24 mL of the cannabinoids oil/ethanol mixture (8 g of cannabinoids oil).

6. Run the following step gradient:

a. flow rate: 100 mL/min

b. gradient 1: 80% methanol and 20% distilled water for 4 CV

c. gradient 2: 85% methanol and 15% distilled water for 7 CV

7. Collect 120 mL fractions for the duration of the run.

8. Run TLC on fractions using 20% diethyl ether and 80% hexane to confirm the identity of cannabinoid fractions. (Fractions collected from 2 CV to 3.5 CV are CBG, fractions collected from 6-9 CV are CBC.)

9. Concentrate the CBG fractions under reduced pressure.

10. Separately concentrate the CBC fractions under reduced pressure.

11. A red oil will remain for the CBG fractions. This can be recrystallized into a solid using 2:1 heptane:CBG.

12. A red oil will remain for CBC fractions. This oil cannot be recrystallized, but is the pure oil form of CBC.

By following this protocol, CBG was obtained having the following properties: ¹H NMR (300 MHz, CDCl3) δ 6.26 (s, 2H), 5.50 (s, 2H), 5.27 (t, 1H), 5.06 (t, H), 3.38 (d, 2H), 2.45 (t, 2H), 2.07 (m, 2H), 1.81 (s, 3H), 1.68 (s, 3H), 1.60 (s, 3H), 1.56 (m, 2H) 1.32 (m, 4H), 0.89 (t, 3H) ESMS: 316.24

Hemp Powder Production

As provided above, the various raffinates, isolates, and compositions may be used to form a dry hemp powder formulation. In additional/alternative aspects, synthetic compounds may be used. Further, other production methods now known or later developed to produce raffinates, isolates, or compositions may be used to derive such compounds. The raffinates, isolates, and compositions may comprise a plurality of cannabinoids.

Table I, below, provides example raffinates which may be used as described more fully herein.

TABLE I Name THC % CBD % CBG % CBC % Other % Raffinate 1 .056 11.78 .34 .34 86.98 Isolate 1 0 0 94 0 6 Raffinate 2 .1 3 0 0 96.9 Isolate 2 .1 99 0 0 .9

As may be seen from Table I, column 1 indicates the name of raffinate or isolate (e.g., Raffinate 1, Isolate 1, Raffinate 2, Isolate 2, etc.), column 2 provides the measured THC percentage by mass, column 3 provides the measured CBD percentage by mass, column 4 provides the measured CBG column by mass, column 5 provides the measured CBC % by mass, and column 6 provides the remaining balance by mass. To use Raffinate 1 as an example, the THC % of Raffinate 1 is 0.056+/−0.001%, the CDB % of Raffinate 1 is 11.78%+/−0.01, the CBG % of Raffinate 1 is 0.34%+/−0.01%, the CBC % is t 0.34+/−0.01%, and the remaining content of the Raffinate 1 is about 86.98%.The Raffinates and isolates of Table I were formed using formed using the processes described above.

With reference to Table II below, Table II indicates various hemp oil extracts/isolates that may be used as described herein to form a hemp powder. These hemp oil extracts/isolates were derived using the systems and methods described herein. The top row of Table II provides column headings. Each subsequent row provides data related to a particular crystalline isolate or cannabis oil. For example row 2 has a profile with THC 00.0%, THCa being 0.00%, CBD 97.57%, CBDa 0.00%, CBN 0.00%, and CBG 0.00%. CBC was not tested for the isolate shown in row 2 (which is indicated by the N/A). It will be noted that were a value is indicated, CBC was tested. Additionally shown is the column “OTHER,” which represents the remaining cannabis products such as other non-measured cannabinoids, terpenes, fatty-acids, proteins, etc, that resulted from the extraction process as described herein. This was calculated by subtracting 100% from the total of the other measured cannabinoids percentages. All percentages shown in Table II are by mass.

With reference to Table II, raw cannabis oil was used as a starting material for the extraction process indicated where the composition number (column 1) is indicated with a superscript of 1. Raw cannabis oil was formed using the LE Method described above. Where no superscript is identified, filtrate oil was used. The starting cannabis material was cannabis sativa with less than 0.3% THC by weight.

Filtrate oil is prepared as follows by decarboxylation, distilling, precipitating, and filtrating raw cannabis oil as follows. For decarboxylation, the raw cannabis oil is transferred to a reactor. This raw cannabis oil was stirred at 120° C. for around two hours+/−30 min. This decarboxylated cannabis extract is then subjected to two distillation passes using a wiped film evaporator. The first distillation pass is completed by heating the decarboxylated cannabis oil at 150° C. under vacuum at ˜1 torr. A second distillation pass is then conducted by heating the decarboxylated cannabis oil that has already undergone a first pass distillation at 180° C. under vacuum at ˜200 mtorr. The distillate collected from this second distillation pass is typically a clear yellow-orange.

The second pass distillate is then subjected to a precipitation using heptane. The collected second pass distillate is placed in a reactor and stirred with heptane at 50° C. for 30 minutes to dissolve the second pass distillate oil. The ratio of heptane to second pass distillate is 2:1 (liters:kg). Upon complete dissolution of second pass distillate the solution is typically a clear yellow color. This solution is then placed in a reactor and cooled to −6° C. for at least 12 hours. A white-yellow precipitate was observed in this second pass distillate/heptane mixture. This CBD precipitate mixture was transferred to a Buchner funnel and recovered as filter cake using vacuum filtration. The filtrate collected from this filtration is typically an orange-yellow solution of heptane. This filtrate solution is then concentrated under reduced pressure at 60° C. to remove the heptane. The remaining filtrate oil is collected as an amber-orange oil.

Column 2 of Table II is labeled “Ext.” Ext indicates the extraction method used to derive the particular hemp oil extract or isolate. Where Column 1 reads “CBD ISO,” the following process is indicated: A prepared column (prepared meaning conditioned with petroleum ether or other suitable solvent) is packed with either raw cannabis oil or filtrate oil (as indicated by the table below) (hereinafter, starting cannabis oil) and petroleum ether (in a ratio of 1.3:1 starting cannabis oil to petroleum ether by pre-mix volume) to form a packed column. A first solvent (6% ethyl ether in petroleum ether by premix volume) is run through the packed column for one column volume (CV) and collected (“a first pre-fraction combination”). An additional 1 CV was collected (“a second pre-fraction combination”). Next, eleven 0.2 CV fractions were collected (“fractions 1-11”). A second solvent (15% ethyl ether in petroleum ether by premix volume) was then run through the column for 4 CVs. During that run, 0.2 CV fractions were collected (“fractions 12-32”). Next, a third solvent (80% ethyl ether in petroleum ether by pre-mix volume) was then run through the column for 4 CVs. During that run, 0.2 CV fractions were collected (“fractions 32-42”). The third solvent continued to run through the column for 10 more CVs and collected (“a first post fraction”).

Where column 2 reads THC Rem indicates the following process: a prepared column was packed with starting cannabis oil and petroleum ether (in a ratio of 5:3 starting cannabis oil in grams to petroleum ether by premix volume milliliters) to form a packed column. A first solvent (ethyl ether and petroleum ether in a ratio of 1:14.9 by premix volume) was run through the column. Two 10 CV fractions were collected (“pre 1 fractions”). Next, the first solvent was run through the column and eighteen 2 CV fractions where collected (“fractions 1-18”). After, a second solvent (ethyl ether and petroleum ether in a ratio of 1.9:13.9 by premix volume) was run through the column. Thirteen 2 CV fractions were collected (“fractions 18-31”). After, a third solvent (ethyl ether and petroleum ether in a ratio of 12.7:3.2 by premix volume) was run through the column. Five 2 CV fractions were collected (“fractions 32-36”). Next, the third solvent was run through the column. Three 8 CV fractions were collected (“Post Fractions 1-3”). It will be appreciated that the first fraction in fractions 1-18 is fraction one, the second is fraction 2, etc.

Where Column 2 reads “CBG/CBC,” the following process is indicated: A prepared reverse phase column was packed with cannabinoid fractions (obtained using the THC Rem Method) and ethanol (in a ratio of 1:1 raw cannabis oil to hot ethanol by pre-mix volume) to form a packed column. A first solvent (20% distilled water in ethanol by pre-mix volume) was run through the packed column for four column volumes (CV). During that run, four 1 CV fractions were collected (“fractions 1-4”). A second solvent (15% distilled water in ethanol by pre-mix volume) was then run through the column for 7 CVs. During that run, seven 1 CV fractions were collected (“fractions 5-11”).

Column 3 indicates the fraction type that was collected from each extraction process to obtain the composition indicated in the row. A fraction type is a fraction or collected group of fractions that has the presence of certain cannabinoids as evidenced by TLC analysis. Using the extraction methods above, the following categories of fraction type were identified: isolate type, raffinate type, delta-9 type, and cannabinoid type.

Using the CBD Iso method, the isolate type is identified by TLC analysis where each fraction is sampled and run in a 20% diethyl ether in petroleum ether mobile phase, and the plate is stained using iodine. Fractions containing cannabidiol (as determined by Rf) are collected and designated as the isolate category. For the CBD ISO method, this was typically the second pre-fraction combination and fractions 1 through 20, though this varied by 0.4 CVs or so depending on the starting cannabis oil.

Using the CBD Iso method, the raffinate category is identified by TLC analysis where each fraction is sampled and run in a 20% diethyl ether in petroleum ether mobile phase, and the plate is stained using iodine. Fractions lacking the presence of CBD and THC (as determined by Rf) by TLC analysis are collected and designated as the raffinate category. For the CBD ISO method, this was typically was the first post fraction though this varied by 0.2 CV or so depending on the starting cannabis oil.

Using the THC Rem method, the isolate category is identified by TLC analysis where each fraction is sampled and run in a 20% diethyl ether in petroleum ether mobile phase, and the plate is stained using iodine. Fractions containing cannabidiol (as determined by Rf) were collected and designated as the isolate category. For THC REM method, this was typically fractions 1 through 20, though varied 0.4 or so column volumes on average depending on the starting cannabis oil.

Using the THC Rem method, raffinate category is identified by TLC analysis where each fraction is sampled and run in a 20% diethyl ether in petroleum ether mobile phase, and the plate is stained using iodine. Fractions lacking the presence of CBD and THC as determined by TLC analysis (as determined by Rf), were collected and designated as the raffinate category. For THC REM method, this was typically Post 1-3, though varied 0.2 CVs or so depending on the starting cannabis oil.

In the THC Rem method, Delta-9 category is identified by TLC analysis where each fraction is sampled and run in a 20% diethyl ether in petroleum ether mobile phase, and the plate is stained using iodine. Fractions containing THC (as determined by Rf) are collected and designated as the Delta-9 category. For THC REM method, this was typically fractions 15 through 24, though this varied by 0.4 or so column volumes depending on the starting raw cannabis oil.

In the THC REM method, cannabinoids category is identified by identified by TLC analysis where each fraction is sampled and run in a 20% diethyl ether in petroleum ether mobile phase, and the plate is stained using iodine. Fractions containing cannabinoids (including CBG, CBC, and CBN as determined by Rf), but in particular lacking the presence of CBD or THC, as determined by TLC analysis are collected and designated as the cannabinoids category. For the THC REM method, this was typically fractions 25 through 36, though this varied by 0.4 or so column volumes depending on the starting raw cannabis oil.

Using the CBG/CBC method, the CBG type is identified by TLC analysis where each fraction is sampled and run in a 20% diethyl ether in petroleum ether mobile phase, and the plate is stained using iodine. Fractions containing CBG (as determined by Rf) are collected and designated as the CBG category. For the CBG/CBC method, this was typically fractions 2 through 4, though this varied by 1 CV or so depending on the starting raw cannabis oil.

Using the CBG/CBC method, the CBC category is identified by TLC analysis where each fraction is sampled and run in a 20% diethyl ether in petroleum ether mobile phase, and the plate is stained using iodine. Fractions containing CBC (as determined by Rf) are collected and designated as the CBC category. For the CBG/CBC method, this was typically fractions 7 and 8, though this varied by 1 CV or so depending on the starting raw cannabis oil.

Column 4 (“Cryst.”) of table indicates whether the fraction(s) were subjected to a crystallization. Where the post processing is a first process, a “1” is indicated. Where it is a second process, a “2” is indicated. Where no post processing was performed, a 0 is indicated.

For the first crystallization post process (indicated by a 1), the following process occurred. The indicated fractions and n-hexane were combined in a 1:2 ratio, stirred, seeded with isolate crystals, and cooled to −6° C. After some time, this forms crude crystals and after some time a layer of orange-yellow hexanes. After an orange-yellow hexane is formed, the resulting liquid was subjected to a rotary vacuum drum to form crude crystals. The crude crystals were rinsed in cold petroleum ether and then decanted and dried. The crude crystals where then again in cold petroleum ether rinsed and decanted, and dried.

Next, the crystals are massed, and a mass of n-hexanes in a ratio of 1:2 crystals to n-hexanes by mass is boiled. This n-hexanes are heated until boil and the crystal are added and stirred until dissolved to form a solution. The solution is then cooled and crude crystals are formed. In the case of Isolate crystals a light-yellow hexane layer is then decanted. The crystals are then rinsed with petroleum ether and decanted. The rinse is repeated. The crystals were ground and heated.

For the second crystallization process (as indicate by a 2), the following process was followed. The indicated fractions and n-hexane were combined in a 1:2 ratio, stirred, seeded with isolate crystals, and cooled to −6° C. After some time, this forms crude crystals and after some time a layer of pink-red hexanes is formed. After a layer of pink-red hexane is formed, the resulting liquid was dried with MgSO₄, filtered, and subjected to a rotary vacuum drum to form crude crystals. The crude crystals were rinsed in cold petroleum ether and then decanted and dried. The crude crystals where then again rinsed and decanted, and dried.

Next, the crystals are massed, and a mass of n-hexanes in a ratio of 1:2 crystals to n-hexanes by mass is boiled. This n-hexanes are heated until boil and the crystal are added and stirred until dissolved to form a solution. The solution is then cooled and crude crystals are formed. In the case of Isolate crystals a light-pink hexane layer is then decanted. The crude crystals are then rinsed with petroleum ether and decanted. The rinse is repeated. The crystals were ground and heated.

TABLE II Fractions Ext. Type Cryst. THC THCa CBD CBDa CBN CBG CBC Other  1 CBD ISO Isolate 1 0.00% 0.00% 97.57% 0.00% 0.00% 0.00% N/A 2.43%  2 CBD ISO Raffinate 0 2.54% 0.00% 60.29% 0.61% 0.16% 1.10% N/A 35.30%  3 CBD ISO Isolate 1 0.00% 0.00% 96.19% 0.00% 0.00% 0.00% N/A 3.81%  4 CBD ISO Isolate 1 0.00% 0.00% 99.86% 0.00% 0.00% 0.00% N/A 0.14%  5 CBD ISO Isolate 1 0.00% 0.00% 97.34% 0.00% 0.00% 0.00% N/A 2.66%  6 CBD ISO Raffinate 0 0.00% 0.00% 10.51% 3.25% 0.00% 4.84% N/A 81.40%  7 CBD ISO Raffinate 0 0.00% 0.00% 0.69% 3.72% 0.00% 0.00% N/A 95.59%  8 CBD ISO Raffinate 0 15.03% 0.00% 49.35% 0.00% 0.75% 1.84% N/A 33.03%  9 CBD ISO Raffinate 0 16.26% 0.00% 42.15% 0.00% 1.04% 1.55% N/A 39.00% 10 CBD ISO Isolate 1 0.00% 0.00% 95.68% 0.00% 0.00% 0.00% N/A 4.32% 11 CBD ISO Isolate 1 0.00% 0.00% 96.85% 0.00% 0.00% 0.00% N/A 3.15%  12¹ THC REM Raffinate 0 0.00% 0.00% 1.13% 64.25% 0.00% 2.27% N/A 32.35% 13 THC REM Cannabinoid 0 0.00% 1.68% 1.34% 2.23% 0.00% 12.56% N/A 82.19%  14¹ THC REM Raffinate 0 0.00% 0.80% 0.30% 81.37% 0.00% 1.04% N/A 16.49% 15 THC REM Isolate 1 0.00% 0.00% 98.91% 0.00% 0.00% 0.00% N/A 1.09% 16 THC REM Isolate 1 0.00% 0.00% 98.73% 0.00% 0.00% 0.00% N/A 1.27% 17 THC REM Cannabinoid 0 0.00% 0.00% 53.73% 1.49% 0.00% 2.80% N/A 41.98% 18 THC REM Raffinate 0 0.00% 0.00% 5.94% 0.32% 0.00% 0.95% N/A 92.79%  19¹ THC REM Cannabinoid 0 0.00% 0.38% 1.73% 62.48% 0.00% 0.66% N/A 34.75% 20 THC REM Isolate 1 0.00% 0.00% 95.80% 0.00% 0.00% 0.00% N/A 4.20% 21 THC REM Raffinate 0 0.16% 0.00% 67.74% 1.13% 0.00% 0.27% N/A 30.70%  22¹ THC REM Raffinate 0 0.00% 6.83% 0.63% 46.80% 0.36% 3.66% N/A 41.72% 23 THC REM Cannabinoid 0 0.00% 0.90% 0.00% 0.98% 0.30% 26.38% N/A 71.44% 24 THC REM Raffinate 0 0.00% 0.00% 0.46% 5.46% 0.00% 6.39% N/A 87.69% 25 THC REM Raffinate 0 4.68% 0.00% 40.60% 1.73% 0.30% 1.01% N/A 51.68%  26¹ THC REM Raffinate 0 0.00% 2.46% 0.00% 74.12% 0.00% 1.12% N/A 22.30% 27 THC REM Isolate 1 0.00% 0.00% 96.19% 0.00% 0.00% 0.00% N/A 3.81% 28 THC REM Isolate 1 0.00% 0.00% 99.97% 0.00% 0.00% 0.00% N/A 0.03% 30 THC REM Isolate 1 0.00% 0.00% 99.18% 0.00% 0.00% 0.00% N/A 0.82% 32 THC REM Isolate 1 0.00% 0.00% 99.12% 0.00% 0.00% 0.00% N/A 0.88% 34 THC REM Raffinate 0 0.00% 0.00% 0.00% 7.76% 0.00% 0.00% N/A 92.24% 35 THC REM Raffinate 0 0.00% 0.00% 0.00% 5.29% 0.00% 0.00% N/A 94.71% 36 THC REM Raffinate 0 0.00% 0.00% 2.81% 0.95% 0.00% 0.54% N/A 95.70% 37 THC REM Raffinate 0 0.00% 0.00% 0.00% 4.77% 0.00% 0.00% N/A 95.23% 38 THC REM Raffinate 0 0.00% 1.66% 0.00% 5.29% 0.00% 0.80% N/A 92.25% 39 THC REM Cannabinoid 0 0.00% 0.00% 0.00% 0.00% 0.00% 23.88% N/A 76.12% 40 THC REM Cannabinoid 0 0.00% 1.13% 0.00% 0.36% 0.30% 19.55% 39.07% 60.41% 41 THC REM Raffinate 0 0.00% 0.48% 0.00% 0.00% 0.00% 0.24% N/A 99.28% 42 CBG/CBC CBC 2 0.00% 0.00% 0.00% 0.00% 0.00% 0.25% 88.19% 11.56% 43 THC REM Cannabinoid 0 0.00% 0.00% 0.57% 0.37% 0.00% 51.54% N/A 47.52% 44 THC REM Cannabinoid 0 0.00% 0.00% 0.78% 0.76% 0.00% 51.11% 13.29% 65.94% 45 CBG/CBC CBG 2 0.00% 0.00% 0.00% 0.00% 0.00% 81.05% N/A 18.95% 46 CBG/CBC CBG 2 0.00% 0.00% 0.00% 0.00% 0.00% 86.34% N/A 13.66% 47 CBG/CBC CBG 2 0.00% 0.00% 0.00% 7.65% 0.00% 82.92% N/A 9.43%

FIG. 13 illustrates a method 1300 for formulating a hemp powder. Method 1300 begins with provide thickening agent 1302. In operation 1302, one or more suitable thickening agents is provided. In aspects of the technology, this may be selected from a group of polysaccharides such as hydrocolloid, cellulose, or maltodextrin may be provided.

The method 1300 proceeds to add flow agent operation 1304. In operation 1304, a flow agent is added to the thickening agent to form a premix. The flow agent may be silica or an organic based flow agent, such as NU-FLOW, or similar substance. As used herein, the combination of thickening agents and flow agents are described as dry powder solids.

The method 1300 optionally proceeds to add isolate 1306. In aspects of the technology, a relative pure (e.g., a cannabinoid crystalate or oil having greater than 92% by mass cannabinoid) isolate is added. This may be added in an amount to adjust the composition of the resulting hemp powder formulation. For example, where it is desired to have more cannabigerol (CBG) as a percentage of mass, an isolate having a relatively high concentration of CBG may be added to the premix to form an enhanced premix. One example of an isolate with a relatively high amount of CBG is Isolate 1 as provided in Table 1. Other examples of isolate additions include those indicated in Table II that have fraction type ISOLATE and/or CBG in column 3. It will be appreciated that more than one isolate may be added during operation 1306.

The method 1300 proceeds to add stabilization agents operation 1308. In operation 1308, one or more stabilization agents may be added to the premix or enhanced premix. Stabilization agents may include anticaking agents, preservatives and drying agents. Examples of such stabilization agents include metal ascorbates (e.g., sodium ascorbate, calcium ascorbate, potassium ascorbate, and magnesium ascorbate), weak organic acids (e.g., lactic acid, citric acid), carbonates (e.g., calcium carbonate) and sodium bicarbonate. In aspects of the technology, stabilization agents may be chosen based on the application of the resulting powder (e.g., edible or non-toxic stabilization agents may be chosen in order to allow the resulting powder to be edible). The addition of the one or more stabilization agents at operation 1308 forms a stabilized aggregate.

The method 1300 proceeds to mix aggregate operation 1310. In operation 1310, the stabilized aggregate formed in operation 1310 is mixed. In aspects of the technology, the mixing occurs rapidly. For example, the mixing may occur by blending the aggregate at about 4000 to 12000 rotations per minute.

The method then proceeds to add raffinate, composition, and/or oil isolate operation 1312. In add raffinate, composition, and/or oil isolate operation 1312, one or more extracts from raw hemp oil are combined to the mixed aggregate formed in operation 1310. The raffinate, composition, and/or isolate may be added slowly so as to prevent clumping. In aspects of the technology, the ratio of raffinate, composition, and/or isolate to dry powder solids (by mass) is below 0.625. In further aspects the technology, the raffinate, composition, and/or isolate to the combination of dry powder solids plus isolates (by mass) is 0.136. During addition of the raffinate, composition, and/or isolate, the dry hemp powder may be subjected to mixing or rapid blending (e.g., 4000 to 12000 rotations per minute). In aspects, prior to or during operation 1312, the mix may be cooled to between −10 degrees Celsius and +10 Celsius. In an aspect, the extracts indicated in Table II with a fraction type RAFFINATE, CBC, and/or Cannabinoid in column 3

Additional Examples

In example 10, a hemp oil raffinate comprising 0.56% THC, 11.78% CBD, 0.34% CBG, and 0.34% CBC, 86.98% other hemp products (by mass) was combined with and equal mass of maltodextrin. The Result was a thick, wax like material.

In example 11, hemp oil raffinate comprising 0.56% THC, 11.78% CBD, 0.34% CBG, and 0.34% CBC, 86.98% other hemp oil product (by mass) was combined with 50% maltodextrin by mass of the raffinate (e.g. a ratio of 2 part raffinate to a part maltodextrin). The Result was a thick, wax like material.

In example 12, hemp oil raffinate comprising 0.56% THC, 11.78% CBD, 0.34% CBG, and 0.34% CBC, 86.98% other hemp oil product (by mass) was combined with and maltodextrin 25% times the mass of the raffinate (e.g. a ratio of four parts raffinate to one part maltodextrin). The result was a thick, mixture similar to that of melted caramel. The texture did not exhibit lumps.

In example 13, hemp oil raffinate comprising 0.56% THC, 11.78% CBD, 0.34% CBG, and 0.34% CBC, 86.98% other hemp oil product (by mass) was combined with and maltodextrin 200% times the mass of the raffinate (e.g. a ratio of one part raffinate to two parts maltodextrin). The result was a homogenous mixture similar to that of cookie dough in both tackiness and texture.

In example 14, hemp oil raffinate comprising 0.56% THC, 11.78% CBD, 0.34% CBG, and 0.34% CBC, 86.98% other hemp oil product (by mass) was combined with and maltodextrin 400% times the mass of the raffinate (e.g. a ratio of one part raffinate to four parts matlodextrin). The result was a homogenous mixture similar to that of damp sand in both tackiness and texture.

In example 15, hemp oil raffinate comprising 0.56% THC, 11.78% CBD, 0.34% CBG, and 0.34% CBC, 86.98% other hemp oil product (by mass) was combined with and maltodextrin 600% times the mass of the raffinate (e.g. a ratio of one part raffinate to four parts matlodextrin). The result was a homogenous mixture similar to that of clumpy flour in both tackiness and texture.

In example 16, hemp oil raffinate consisting 0.56% THC, 11.78% CBD, 0.34% CBG, and 0.34% CBC, 86.98% other hemp oil product (by mass) was combined with about 99% pure CBD isolate to make an oil that was 75% CBD by mass. The resulting oil was mixed with maltodextrin 350% times the mass of the raffinate (e.g. a ratio of one part mixed oil to 3.5 parts matlodextrin). The result was a wet sand consistency, similar to that of play sand in both tackiness and texture.

In example 17, silica was added to the mixture in a ratio of 4 parts mixture to 1 part silica to example 16. The resulting powder had a slightly better flow and consistency

In example 18, the CBD isolate of at about least 99% pure CBD was added to the mixture of example 16.

In example 19, a mixture comprising of 25.7% hemp oil raffinate (the hemp oil being 0.45% THC, 61.00% CBD, 38.55% other hemp oil product (by mass)), 34.3% maltodextrin, 32.9% CBD isolate (such as isolate 2 provided in table 1 above), and 6.9% silica was formed. The result was a homogenous mixture similar to that of flour of dry sand in texture and tackiness.

In example 20, a mixture of 13.7% hemp oil raffinate (0.056% THC, 11.78% CBD, 0.34% CBG, and 0.34% CBC, 86.98% other hemp oil product (by mass)), 0.1% hemp oil raffinate (such as raffinate 2 provided in table 2 above), 49.0% of a CBD isolate (such as isolate 2 provided in table 1 above), 6% silica, and 30.2% maltodextrin was formed. The result was a homogenous mixture similar to that of flour in texture and tackiness.

In example 21, 52.55% CBD isolate (by mass) (greater than 99% purity), 40.98% maltodextrin (by mass), 1.96% hemp oil raffinate (by mass) (the hemp oil raffinate comprising, by mass, 7.76% CBDA, 0.00% THCa 0.00%, THC, 0.00% CBD, 0.00% CBN, 0.00% CBG, and the remainder other hemp oil extract), 1.96% silica (by mass), 1.27% CBC oil (by mass) (comprising, by mass, 0.25% CBG, 88.19% CBC, 0.00% CBCA, 0.00% CBL, 0.00% CBD, 0.00% CBDA, 0.00% CBDV, 0.00% CBDVA, 0.00% CBN, 0.00% CBNA, >0.3 THC, and the remainder other hemp oil extract), 1.16% CBG composition I (by mass) (comprising 86.34% CBG, 0.53% THC, 0.00% THCa, 0.00% CBDa, 0.00% CBD, 0.00% CBN, and the remainder other hemp oil extract), and 0.12% CBG composition II (7.65% CBD, 82.92% CBG, 0.00% THCa, 0.00% THC, 0.00% CBDa, 0.00% CBN, the remainder other hemp oil extract) was combined. These compounds were combined in a high-speed electric grain grinder. The result was a homogeneous, tan powder, similar in texture to brown sugar. Cannabinoid content analysis identified 51.58% CBD, 0.94% CBG (by mass) (other cannabinoids not measured).

In example 22, 51.39% CBD isolate (by mass) (greater than 99% purity), 43.49% maltodextrin (by mass), 2.00% hemp oil raffinate (by mass) (the hemp oil raffinate comprising 5.29% CBDA, 0.00% THCa, 0.00% THC, 0.00% CBDa, 0.00% CBD, 0.00% CBN, CBG, and the remainder other hemp oil extract), 2.00% silica (by mass), 0.90% Cannabinoid Oil (by mass) (comprising 0.36% CBD, 19.55% CBG, 39.07% CBC, and 1.13% THC, 0.30% CBN, 0.37% THCV, and 0.00% CBCA, 0.00% CBL, 0.00% CBDA, 0.00% CBDV, 0.00% CBDVA, 0.00% CBGA, 0.00% CBNA, 0.00% Delta8-THC, 0.00% THCA-A, 0.00% THCVA, and the remainder other hemp oil extract) and 0.22% CBG composition (7.65% CBD, 82.92% CBG, 0.00% THCa, 0.00% THC, 0.00% CBDa, 0.00% CBN, and the remainder other hemp oil extract) is combined. It will be appreciated that these compounds were combined in a high-speed electric grain grinder. The result was a homogeneous, tan powder, similar in texture to brown sugar. Cannabinoid content analysis identified 52.56% CBD, 0.36% CBG (other cannabinoids not measured). It will be appreciated that other hemp oil product and other hemp oil extract represents the other non-measured cannabinoids, terpenes, fatty-acids, etc, that resulted from the extraction process as described herein. 

What is claimed:
 1. A cannabinoid concentrate composition comprising: a. a plant extract comprising: less than about 0.6 percent of tetrahydrocannabinol by weight of the plant extract; greater than about 10 percent of cannabidiol by weight of the plant extract; and at least about 85% other plant extract material; b. at least one thickening agent selected from the group consisting of hydrocolloid, cellulose, and maltodextrin, wherein the weight of the at least one thickening agent is at least 400% that of the weight of the plant extract; and c. a flow agent in an amount between about 1.9% and 6.9% of the total concentrate composition; wherein the cannabinoid concentrate composition is a dry, free-flowing powder.
 2. The composition of claim 1, further comprising a stabilizing agent selected from the group of sodium ascorbate, calcium ascorbate, potassium ascorbate, magnesium ascorbate, lactic acid, citric acid, calcium carbonate, and sodium bicarbonate.
 3. The composition of claim 1, wherein the other plant extract material comprises about 90 wt. % of a combination of cannabichromene and cannabigerol.
 4. The composition of claim 1, wherein the composition is substantially free of tetrahydrocannabinol.
 5. The composition of claim 1, further comprising synthetic cannabinoids.
 6. The composition of claim 1, wherein the other plant extract material comprises about 5 to about 25 wt. % of fatty acids and/or terpenes.
 7. The composition of claim 1, wherein the flow agent comprises silica. 